WINR / Simplicity Esports and Gaming Company - Pengajuan SECLaporan Tahunan, Pernyataan Proksi

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 Date of Report (Date of earliest event reported) April 24, 2024 (August 5, 2024) SI

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 Date of Report (Date of earliest event reported) April 24, 2024 (August 5, 2024) SIMPLICITY ESPORTS AND GAMING COMPANY (Exact name of registrant as specified in its charter) Delaware 001-38188 82-1231127 (State or other jurisdiction

SIMPLICITY ESPORTS AND GAMING COMPANY AMENDMENT TO BYLAWS

Exhibit 3.3 SIMPLICITY ESPORTS AND GAMING COMPANY AMENDMENT TO BYLAWS This Amendment to the Bylaws (the “Bylaws”) of Simplicity Esports and Gaming Company, as adopted by the Board of Directors pursuant to Delaware General Corporation Law, Section 141(f) and Section 4.5 of said Bylaws, is effective as of the 5th day of August, 2024. Article II, Section 2.9 of the Bylaws, entitled “Consents in Lieu

Assignment Agreement

Exhibit 3.1 Assignment Agreement This Assignment Agreement (the “Agreement”) is made by and between James Hiza, an individual (the “Assignee”) and Roman Franklin, an individual (the “Assignor”), effective April 12, 2024. The Assignor and the Assignee are sometimes referred to in this Agreement singly as a “Party” or collectively as the “Parties”. WHEREAS, the Assignor is the holder of one share of

CERTIFICATE OF AMENDMENT TO CERTIFICATE OF DESIGNATIONS OF PREFERENCES AND RIGHTS OF SERIES X CONVERTIBLE PREFERRED STOCK OF SIMPLICITY ESPORTS AND GAMING COMPANY

Exhibit 4.2 CERTIFICATE OF AMENDMENT TO CERTIFICATE OF DESIGNATIONS OF PREFERENCES AND RIGHTS OF SERIES X CONVERTIBLE PREFERRED STOCK OF SIMPLICITY ESPORTS AND GAMING COMPANY Simplicity Esports and Gaming Company, a corporation organized and existing under the laws of the State of Delaware (hereinafter called the “Corporation”), does hereby certify as follows: FIRST: The Board of Directors of the

EX-4.1

Exhibit 4.1

CERTIFICATE OF AMENDMENT TO THE THIRD AMENDED AND RESTATED CERTIFICATE OF INCORPORATION OF SIMPLICITY ESPORTS AND GAMING COMPANY

Exhibit 3.2 CERTIFICATE OF AMENDMENT TO THE THIRD AMENDED AND RESTATED CERTIFICATE OF INCORPORATION OF SIMPLICITY ESPORTS AND GAMING COMPANY Simplicity Esports and Gaming Company (the “Corporation”), a corporation organized and existing under and by virtue of the provisions of the General Corporation Law of the State of Delaware (the “General Corporation Law”), does hereby certify: 1. The current

Securities Purchase Agreement by and among the registrant and 1800 Diagonal Lending, LLC, dates as of June 13,2023.

Exhibit 10.1

Convertible Promissory Note by and among the registrant and 1800 Diagonal Lending, LLC, dates as of June 13, 2023.

Exhibit 10.2

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 Date of Report (Date of earliest event reported) June 13, 2023 SIMPLICITY ESPORTS A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 Date of Report (Date of earliest event reported) June 13, 2023 SIMPLICITY ESPORTS AND GAMING COMPANY (Exact name of registrant as specified in its charter) Delaware 001-38188 82-1231127 (State or other jurisdiction (Commission (IRS E

Secured Convertible Promissory Note, dated as of April 17, 2023, issued by the registrant in favor of FirstFire Global Opportunities Fund LLC.

Exhibit 10.10

Securities Purchase Agreement, dated as of April 17, 2023, by and between the registrant, Ionic Ventures, LLC and FirstFire Global Opportunities Fund LLC.

Exhibit 10.8 SECURITIES PURCHASE AGREEMENT This SECURITIES PURCHASE AGREEMENT (the “Agreement”), dated as of April 17, 2023, by and between SIMPLICITY ESPORTS AND GAMING COMPANY, a Delaware corporation, with headquarters located at 7000 West Palmetto Park Road, Suite 505, Boca Raton, Florida 33433 (the “Company”), and the investors who are signatories to this Agreement and scheduled on Schedule A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q ☒ QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended February 28, 2023 ☐ TRANSITION REPORT PURSUANT

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q ☒ QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended February 28, 2023 or ☐ TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission File Number: 001-38188 SIMPLICITY ESPORT

Secured Convertible Promissory Note, dated as of April 17, 2023, issued by the registrant in favor of Ionic Ventures, LLC.

Exhibit 10.9

Convertible Promissory Note, dated as of March 8, 2023, issued by the registrant in favor of Ionic Ventures, LLC.

Exhibit 10.2

Securities Purchase Agreement, dated as of March 8, 2023, by and between the registrant and FirstFire Global Opportunities Fund, LLC.

Exhibit 10.3

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (date of earliest event reported): March 8, 2023 SIMPLICITY ESPORTS

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (date of earliest event reported): March 8, 2023 SIMPLICITY ESPORTS AND GAMING COMPANY (Exact name of registrant as specified in its charter) Delaware 001-38188 82-1231127 (State or other jurisdiction of incorporation)

Convertible Promissory Note, dated as of March 8, 2023, issued by the registrant in favor of FirstFire Global Opportunities Fund, LLC.

Exhibit 10.4

Securities Purchase Agreement, dated as of March 8, 2023, by and between the registrant and Ionic Ventures, LLC.

Exhibit 10.1

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 12b-25 SEC FILE NUMBER 001-38188 NOTIFICATION OF LATE FILING CUSIP NUMBER (Check one): ☐ Form 10-K ☐ Form 20-F ☐ Form 11-K ☒ Form 10-Q ☐ Form 10-D ☐ Form ☐ N-CEN ☐ Form N-CSR For Period Ended: February 28, 2023 ☐ Transition Report on Form 10-K ☐ Transition Report on Form 20-F ☐ Transition Report on Form 11-K ☐ Transition

Amendment No. 2 to Exchange Agreement, dated as of March 10, 2023, by and among the registrant, Diverted River Technology, LLC, the member(s) of Diverted River Technology, LLC from time to time and Zachary Johnson, as the Members’ representative.

Exhibit 10.3 Amendment No. 2 to Exchange Agreement Dated as of March 10, 2023 This Amendment No. 1 to Exchange Agreement (this “Amendment”) is entered into as of the date first set forth above (the “Amendment Date”) by and between (i) Simplicity Esports and Gaming Company, a Delaware corporation (the “Company”); (ii) Diverted River Technology, LLC, an Indiana limited liability company (“DRT”), and

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (date of earliest event reported): March 10, 2023 SIMPLICITY ESPORTS

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (date of earliest event reported): March 10, 2023 SIMPLICITY ESPORTS AND GAMING COMPANY (Exact name of registrant as specified in its charter) Delaware 001-38188 82-1231127 (State or other jurisdiction of incorporation

Simplicity Esports

Exhibit 99.1 Simplicity Esports Signs Agreement to Convert Promissory Notes into 5% Common Stock Ownership and Extension to Exchange Agreement with Software Company Diverted River Technology, LLC The agreement converts over $6.1 million in debt into 5% common stock ownership in the combined companies at closing of the Diverted River Technology, LLC (“Diverted River”) exchange agreement. Boca Raton

Letter Agreement, dated as of March 21, 2023, by and among the registrant, Ionic Ventures, LLC, FirstFire Global Opportunities Fund, Jefferson Street Capital, Labrys Fund, GS Capital Partners, and Lucas Ventures & LGH Investments.

Simplicity Esports and Gaming Company Exhibit 10.4 March 21, 2023 Simplicity Esports And Gaming Company 7000 W. Palmetto Park Road – Suite 505 Boca Raton, FL 33433 Re: Agreement to Convert Convertible Promissory Notes Reference is made to the convertible promissory notes issued by Simplicity Esports And Gaming Company (“WINR” or the “Company”) and enumerated on Schedule A attached hereto (collecti

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q ☒ QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended November 30, 2022 ☐ TRANSITION REPORT PURSUANT

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q ☒ QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended November 30, 2022 or ☐ TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission File Number: 001-38188 SIMPLICITY ESPORT

Securities Purchase Agreement, dated as of January 30, 2023, by and between the registrant and FirstFire Global Opportunities Fund, LLC.

Exhibit 10.3 SECURITIES PURCHASE AGREEMENT This SECURITIES PURCHASE AGREEMENT (the “Agreement”), dated as of January 30, 2023, by and between SIMPLICITY ESPORTS AND GAMING COMPANY, a Delaware corporation, with headquarters located at 7000 West Palmetto Park Road, Suite 505, Boca Raton, Florida 33433 (the “Company”), and FirstFire Global Opportunities Fund, LLC, (the “Buyer”). WHEREAS: A. The Compa

Securities Purchase Agreement, dated as of January 30, 2023, by and between the registrant and Ionic Ventures, LLC.

Exhibit 10.1 SECURITIES PURCHASE AGREEMENT This SECURITIES PURCHASE AGREEMENT (the “Agreement”), dated as of January 30, 2023, by and between SIMPLICITY ESPORTS AND GAMING COMPANY, a Delaware corporation, with headquarters located at 7000 West Palmetto Park Road, Suite 505, Boca Raton, Florida 33433 (the “Company”), and Ionic Ventures, LLC, (the “Buyer”). WHEREAS: A. The Company and the Buyer are

Convertible Promissory Note, dated as of January 30, 2023, issued by the registrant in favor of Ionic Ventures, LLC.

Exhibit 10.2 NEITHER THE ISSUANCE AND SALE OF THE SECURITIES REPRESENTED BY THIS CERTIFICATE NOR THE SECURITIES INTO WHICH THESE SECURITIES ARE CONVERTIBLE HAVE BEEN REGISTERED UNDER THE SECURITIES ACT OF 1933, AS AMENDED, OR APPLICABLE STATE SECURITIES LAWS. THE SECURITIES MAY NOT BE OFFERED FOR SALE, SOLD, TRANSFERRED OR ASSIGNED (I) IN THE ABSENCE OF (A) AN EFFECTIVE REGISTRATION STATEMENT FOR

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (date of earliest event reported): January 30, 2023 SIMPLICITY ESPOR

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (date of earliest event reported): January 30, 2023 SIMPLICITY ESPORTS AND GAMING COMPANY (Exact name of registrant as specified in its charter) Delaware 001-38188 82-1231127 (State or other jurisdiction of incorporati

Convertible Promissory Note, dated as of January 30, 2023, issued by the registrant in favor of FirstFire Global Opportunities Fund, LLC.

Exhibit 10.4 NEITHER THE ISSUANCE AND SALE OF THE SECURITIES REPRESENTED BY THIS CERTIFICATE NOR THE SECURITIES INTO WHICH THESE SECURITIES ARE CONVERTIBLE HAVE BEEN REGISTERED UNDER THE SECURITIES ACT OF 1933, AS AMENDED, OR APPLICABLE STATE SECURITIES LAWS. THE SECURITIES MAY NOT BE OFFERED FOR SALE, SOLD, TRANSFERRED OR ASSIGNED (I) IN THE ABSENCE OF (A) AN EFFECTIVE REGISTRATION STATEMENT FOR

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (date of earliest event reported): January 20, 2023 SIMPLICITY ESPOR

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (date of earliest event reported): January 20, 2023 SIMPLICITY ESPORTS AND GAMING COMPANY (Exact name of registrant as specified in its charter) Delaware 001-38188 82-1231127 (State or other jurisdiction of incorporati

Certificate of Amendment, filed on January 20, 2026.

Exhibit 3.1

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549

NT 10-Q 1 formnt10-q.htm UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 12b-25 SEC FILE NUMBER 001-38188 NOTIFICATION OF LATE FILING CUSIP NUMBER (Check one): ☐ Form 10-K ☐ Form 20-F ☐ Form 11-K ☒ Form 10-Q ☐ Form 10-D ☐ Form ☐ N-CEN ☐ Form N-CSR For Period Ended: November 30, 2022 ☐ Transition Report on Form 10-K ☐ Transition Report on Form 20-F ☐ Transition Report o

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14C Information Statement Pursuant to Section 14 (c) of the Securities Exchange Act of 1934

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14C Information Statement Pursuant to Section 14 (c) of the Securities Exchange Act of 1934 Check the appropriate box: ☐ Preliminary Information Statement ☐ Confidential, for Use of the Commission Only (as permitted by Rule 14c-5 (d)(2)) ☒ Definitive Information Statement SIMPLICITY ESPORTS AND GAMING COMPANY (Name of

Amendment No. 1 to Exchange Agreement, dated as of December 15, 2022, by and among the registrant, Diverted River Technology, LLC, the member(s) of Diverted River Technology, LLC from time to time and Zachary Johnson, as the Members’ representative (incorporated by reference to Exhibit 10.1 to the registrant’s Current Report on Form 8-K filed on December 16, 2022).

Exhibit 10.1 Amendment No. 1 to Exchange Agreement Dated as of December 15, 2022 This Amendment No. 1 to Exchange Agreement (this “Amendment”) is entered into as of the date first set forth above (the “Amendment Date”) by and between (i) Simplicity Esports and Gaming Company, a Delaware corporation (the “Company”); (ii) Diverted River Technology, LLC, an Indiana limited liability company (“DRT”),

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (date of earliest event reported): December 15, 2022 SIMPLICITY ESPO

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (date of earliest event reported): December 15, 2022 SIMPLICITY ESPORTS AND GAMING COMPANY (Exact name of registrant as specified in its charter) Delaware 001-38188 82-1231127 (State or other jurisdiction of incorporat

Departure of Directors or Certain Officers; Election of Directors; Appointment of Certain Officers; Compensatory Arrangements of Certain Officers

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (date of earliest event reported): November 9, 2022 SIMPLICITY ESPORTS AND GAMING COMPANY (Exact name of registrant as specified in its charter) Delaware 001-38188 82-1231127 (State or other jurisdiction of incorporati

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q ☒ QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended August 31, 2022 ☐ TRANSITION REPORT PURSUANT TO

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q ☒ QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended August 31, 2022 or ☐ TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission File Number: 001-38188 SIMPLICITY ESPORTS

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14C Information Statement Pursuant to Section 14 (c) of the Securities Exchange Act of 1934

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14C Information Statement Pursuant to Section 14 (c) of the Securities Exchange Act of 1934 Check the appropriate box: ☒ Preliminary Information Statement ☐ Confidential, for Use of the Commission Only (as permitted by Rule 14c-5 (d)(2)) ☐ Definitive Information Statement SIMPLICITY ESPORTS AND GAMING COMPANY (Name of

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 12b-25 SEC FILE NUMBER 001-38188 NOTIFICATION OF LATE FILING CUSIP NUMBER (Check one): ? Form 10-K ? Form 20-F ? Form 11-K ? Form 10-Q ? Form 10-D ? Form ? N-CEN ? Form N-CSR For Period Ended: August 31, 2022 ? Transition Report on Form 10-K ? Transition Report on Form 20-F ? Transition Report on Form 11-K ? Transition Re

Simplicity Esports

Exhibit 99.1 Simplicity Esports Signs Exchange Agreement with Software Company Diverted River Technology, LLC Diverted River is an Entertainment Technology Organization (?ETO?) started by the founders of ggCircuit. ggCircuit was sold to NASDAQ listed Esports Entertainment Group for $26,000,000 in 2021. Boca Raton, Florida ? September 29, 2022 (GLOBE NEWSWIRE) ? Simplicity Esports and Gaming Compan

Regulation FD Disclosure, Financial Statements and Exhibits

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (date of earliest event reported): September 29, 2022 SIMPLICITY ESPORTS AND GAMING COMPANY (Exact name of registrant as specified in its charter) Delaware 001-38188 82-1231127 (State or other jurisdiction of incorpora

Entry into a Material Definitive Agreement, Financial Statements and Exhibits

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (date of earliest event reported): September 28, 2022 SIMPLICITY ESPORTS AND GAMING COMPANY (Exact name of registrant as specified in its charter) Delaware 001-38188 82-1231127 (State or other jurisdiction of incorpora

Exchange Agreement, dated as of September 28, 2022, by and among the registrant, Diverted River Technology, LLC, the member(s) of Diverted River Technology, LLC from time to time and Zachary Johnson, as the Members’ representative.

Exhibit 10.1 Exchange Agreement BY AND AMONG Simplicity Esports and Gaming Company, Diverted River Technology, LLC, The Member(s) of Diverted River Technology, LLC from Time to Time And Zachary Johnson as the Members? Representative TABLE OF CONTENTS PAGE ARTICLE I. Definitions and Interpretations 1 Section 1.01 Definitions 1 Section 1.02 Interpretive Provisions 7 ARTICLE II. The Transactions 8 Se

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 Form 10-K ☒ ANNUAL REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the fiscal year ended May 31, 2022 ☐ TRANSITION REPORT PURSUANT TO SECTION 13

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 Form 10-K ? ANNUAL REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the fiscal year ended May 31, 2022 ? TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission file number: 001-38188 SIMPLICITY ESPORTS AND GAMING COM

List of Subsidiaries

EXHIBIT 21.1 List of Subsidiaries of Simplicity Esports and Gaming Company Entity Name Place of Organization Simplicity Esports, LLC * Florida PLAYlive Nation, Inc * Delaware PLAYlive Nation Holdings, LLC * Delaware Simplicity One Brasil Ltda ** Brazil Simplicity Happy Valley, LLC *** Oregon Simplicity Redmond, LLC *** Washington Simplicity El Paso, LLC**** Texas Simplicity Union Gap, LLC * Washin

Entry into a Material Definitive Agreement, Financial Statements and Exhibits

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (date of earliest event reported): September 13, 2022 SIMPLICITY ESPORTS AND GAMING COMPANY (Exact name of registrant as specified in its charter) Delaware 001-38188 82-1231127 (State or other jurisdiction of incorpora

Securities Purchase Agreement, dated as of September 13, 2022, by and between the registrant and GS Capital Partners LLC (incorporated by reference to Exhibit 10.1 to the Company’s Current Report on Form 8-K filed with the SEC on September 19, 2022).

Exhibit 10.1 SECURITIES PURCHASE AGREEMENT This SECURITIES PURCHASE AGREEMENT (the ?Agreement?), dated as of September 13, 2022, by and between SIMPLICITY ESPORTS AND GAMING COMPANY, a Delaware corporation, with headquarters located at 7000 West Palmetto Park Road, Suite 505, Boca Raton, Florida 33433 (the ?Company?), and GS Capital Partners LLC, (the ?Buyer?). WHEREAS: A. The Company and the Buye

Common Stock Purchase Warrant, dated as of September 13, 2022, issued by the registrant in favor of GS Capital Partners LLC (incorporated by reference to Exhibit 10.3 to the Company’s Current Report on Form 8-K filed with the SEC on September 19, 2022).

Exhibit 10.3 NEITHER THIS SECURITY NOR THE SECURITIES FOR WHICH THIS SECURITY IS EXERCISABLE HAVE BEEN REGISTERED WITH THE SECURITIES AND EXCHANGE COMMISSION OR THE SECURITIES COMMISSION OF ANY STATE IN RELIANCE UPON AN EXEMPTION FROM REGISTRATION UNDER THE SECURITIES ACT OF 1933, AS AMENDED (THE ?SECURITIES ACT?), AND, ACCORDINGLY, MAY NOT BE OFFERED OR SOLD EXCEPT PURSUANT TO AN EFFECTIVE REGIST

Convertible Promissory Note, dated as of September 13, 2022, issued by the registrant in favor of GS Capital Partners LLC (incorporated by reference to Exhibit 10.2 to the Company’s Current Report on Form 8-K filed with the SEC on September 19, 2022).

Exhibit 10.2 NEITHER THE ISSUANCE AND SALE OF THE SECURITIES REPRESENTED BY THIS CERTIFICATE NOR THE SECURITIES INTO WHICH THESE SECURITIES ARE CONVERTIBLE HAVE BEEN REGISTERED UNDER THE SECURITIES ACT OF 1933, AS AMENDED, OR APPLICABLE STATE SECURITIES LAWS. THE SECURITIES MAY NOT BE OFFERED FOR SALE, SOLD, TRANSFERRED OR ASSIGNED (I) IN THE ABSENCE OF (A) AN EFFECTIVE REGISTRATION STATEMENT FOR

Securities Purchase Agreement, dated as of September 8, 2022, by and between the registrant and Jefferson Street Capital, LLC (incorporated by reference to Exhibit 10.4 to the Company’s Current Report on Form 8-K filed with the SEC on September 15, 2022).

Exhibit 10.4 SECURITIES PURCHASE AGREEMENT This SECURITIES PURCHASE AGREEMENT (the ?Agreement?), dated as of September 8, 2022, by and between SIMPLICITY ESPORTS AND GAMING COMPANY, a Delaware corporation, with headquarters located at 7000 West Palmetto Park Road, Suite 505, Boca Raton, Florida 33433 (the ?Company?), and Jefferson Street Capital, LLC, (the ?Buyer?). WHEREAS: A. The Company and the

Securities Purchase Agreement, dated as of September 8, 2022, by and between the registrant and Ionic Ventures, LLC (incorporated by reference to Exhibit 10.1 to the Company’s Current Report on Form 8-K filed with the SEC on September 15, 2022).

Exhibit 10.1 SECURITIES PURCHASE AGREEMENT This SECURITIES PURCHASE AGREEMENT (the ?Agreement?), dated as of September 8, 2022, by and between SIMPLICITY ESPORTS AND GAMING COMPANY, a Delaware corporation, with headquarters located at 7000 West Palmetto Park Road, Suite 505, Boca Raton, Florida 33433 (the ?Company?), and Ionic Ventures, LLC, (the ?Buyer?). WHEREAS: A. The Company and the Buyer are

Convertible Promissory Note, dated as of September 8, 2022, issued by the registrant in favor of Ionic Ventures, LLC (incorporated by reference to Exhibit 10.2 to the Company’s Current Report on Form 8-K filed with the SEC on September 15, 2022).

Exhibit 10.2 NEITHER THE ISSUANCE AND SALE OF THE SECURITIES REPRESENTED BY THIS CERTIFICATE NOR THE SECURITIES INTO WHICH THESE SECURITIES ARE CONVERTIBLE HAVE BEEN REGISTERED UNDER THE SECURITIES ACT OF 1933, AS AMENDED, OR APPLICABLE STATE SECURITIES LAWS. THE SECURITIES MAY NOT BE OFFERED FOR SALE, SOLD, TRANSFERRED OR ASSIGNED (I) IN THE ABSENCE OF (A) AN EFFECTIVE REGISTRATION STATEMENT FOR

Common Stock Purchase Warrant, dated as of September 8, 2022, issued by the registrant in favor of Ionic Ventures, LLC (incorporated by reference to Exhibit 10.3 to the Company’s Current Report on Form 8-K filed with the SEC on September 15, 2022).

Exhibit 10.3 NEITHER THIS SECURITY NOR THE SECURITIES FOR WHICH THIS SECURITY IS EXERCISABLE HAVE BEEN REGISTERED WITH THE SECURITIES AND EXCHANGE COMMISSION OR THE SECURITIES COMMISSION OF ANY STATE IN RELIANCE UPON AN EXEMPTION FROM REGISTRATION UNDER THE SECURITIES ACT OF 1933, AS AMENDED (THE ?SECURITIES ACT?), AND, ACCORDINGLY, MAY NOT BE OFFERED OR SOLD EXCEPT PURSUANT TO AN EFFECTIVE REGIST

Securities Purchase Agreement, dated as of July 14, 2022, by and between the registrant and FirstFire Global Opportunities Fund, LLC (incorporated by reference to Exhibit 10.7 to the Company’s Current Report on Form 8-K filed with the SEC on September 15, 2022).

Exhibit 10.7 SECURITIES PURCHASE AGREEMENT This SECURITIES PURCHASE AGREEMENT (the ?Agreement?), dated as of September 8, 2022, by and between SIMPLICITY ESPORTS AND GAMING COMPANY, a Delaware corporation, with headquarters located at 7000 West Palmetto Park Road, Suite 505, Boca Raton, Florida 33433 (the ?Company?), and FIRSTFIRE GLOBAL OPPORTUNITIES FUND LLC, (the ?Buyer?). WHEREAS: A. The Compa

Convertible Promissory Note, dated as of July 14, 2022, issued by the registrant in favor of FirstFire Global Opportunities Fund, LLC (incorporated by reference to Exhibit 10.8 to the Company’s Current Report on Form 8-K filed with the SEC on September 15, 2022).

Exhibit 10.8 NEITHER THE ISSUANCE AND SALE OF THE SECURITIES REPRESENTED BY THIS CERTIFICATE NOR THE SECURITIES INTO WHICH THESE SECURITIES ARE CONVERTIBLE HAVE BEEN REGISTERED UNDER THE SECURITIES ACT OF 1933, AS AMENDED, OR APPLICABLE STATE SECURITIES LAWS. THE SECURITIES MAY NOT BE OFFERED FOR SALE, SOLD, TRANSFERRED OR ASSIGNED (I) IN THE ABSENCE OF (A) AN EFFECTIVE REGISTRATION STATEMENT FOR

Entry into a Material Definitive Agreement, Financial Statements and Exhibits

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (date of earliest event reported): September 8, 2022 SIMPLICITY ESPORTS AND GAMING COMPANY (Exact name of registrant as specified in its charter) Delaware 001-38188 82-1231127 (State or other jurisdiction of incorporat

Common Stock Purchase Warrant, dated as of July 14, 2022, issued by the registrant in favor of FirstFire Global Opportunities Fund, LLC (incorporated by reference to Exhibit 10.9 to the Company’s Current Report on Form 8-K filed with the SEC on September 15, 2022).

Exhibit 10.9 NEITHER THIS SECURITY NOR THE SECURITIES FOR WHICH THIS SECURITY IS EXERCISABLE HAVE BEEN REGISTERED WITH THE SECURITIES AND EXCHANGE COMMISSION OR THE SECURITIES COMMISSION OF ANY STATE IN RELIANCE UPON AN EXEMPTION FROM REGISTRATION UNDER THE SECURITIES ACT OF 1933, AS AMENDED (THE ?SECURITIES ACT?), AND, ACCORDINGLY, MAY NOT BE OFFERED OR SOLD EXCEPT PURSUANT TO AN EFFECTIVE REGIST

Convertible Promissory Note, dated as of September 8, 2022, issued by the registrant in favor of Jefferson Street Capital, LLC (incorporated by reference to Exhibit 10.5 to the Company’s Current Report on Form 8-K filed with the SEC on September 15, 2022).

Exhibit 10.5 NEITHER THE ISSUANCE AND SALE OF THE SECURITIES REPRESENTED BY THIS CERTIFICATE NOR THE SECURITIES INTO WHICH THESE SECURITIES ARE CONVERTIBLE HAVE BEEN REGISTERED UNDER THE SECURITIES ACT OF 1933, AS AMENDED, OR APPLICABLE STATE SECURITIES LAWS. THE SECURITIES MAY NOT BE OFFERED FOR SALE, SOLD, TRANSFERRED OR ASSIGNED (I) IN THE ABSENCE OF (A) AN EFFECTIVE REGISTRATION STATEMENT FOR

Common Stock Purchase Warrant, dated as of September 8, 2022, issued by the registrant in favor of Jefferson Street Capital, LLC (incorporated by reference to Exhibit 10.6 to the Company’s Current Report on Form 8-K filed with the SEC on September 15, 2022).

Exhibit 10.6 NEITHER THIS SECURITY NOR THE SECURITIES FOR WHICH THIS SECURITY IS EXERCISABLE HAVE BEEN REGISTERED WITH THE SECURITIES AND EXCHANGE COMMISSION OR THE SECURITIES COMMISSION OF ANY STATE IN RELIANCE UPON AN EXEMPTION FROM REGISTRATION UNDER THE SECURITIES ACT OF 1933, AS AMENDED (THE ?SECURITIES ACT?), AND, ACCORDINGLY, MAY NOT BE OFFERED OR SOLD EXCEPT PURSUANT TO AN EFFECTIVE REGIST

Unregistered Sales of Equity Securities, Amendments to Articles of Incorporation or Bylaws; Change in Fiscal Year, Financial Statements and Exhibits

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (date of earliest event reported): August 23, 2022 SIMPLICITY ESPORTS AND GAMING COMPANY (Exact name of registrant as specified in its charter) Delaware 001-38188 82-1231127 (State or other jurisdiction of incorporatio

Certificate of Designations of the Series X Preferred Stock, filed with the Delaware Secretary of State on August 23, 2022 (incorporated by reference to Exhibit 3.1 to the registrant’s Current Report on Form 8-K filed on September 2, 2022).

Exhibit 3.1

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 12b-25 SEC FILE NUMBER 001-38188 NOTIFICATION OF LATE FILING CUSIP NUMBER (Check one): ? Form 10-K ? Form 20-F ? Form 11-K ?Form 10-Q ? Form 10-D ? Form ? N-CEN ? Form N-CSR For Period Ended: May 31, 2022 ? Transition Report on Form 10-K ? Transition Report on Form 20-F ? Transition Report on Form 11-K ? Transition Report

Common Stock Purchase Warrant, dated as of July 14, 2022, issued by the registrant in favor of FirstFire Global Opportunities Fund, LLC.

Exhibit 10.9 NEITHER THIS SECURITY NOR THE SECURITIES FOR WHICH THIS SECURITY IS EXERCISABLE HAVE BEEN REGISTERED WITH THE SECURITIES AND EXCHANGE COMMISSION OR THE SECURITIES COMMISSION OF ANY STATE IN RELIANCE UPON AN EXEMPTION FROM REGISTRATION UNDER THE SECURITIES ACT OF 1933, AS AMENDED (THE ?SECURITIES ACT?), AND, ACCORDINGLY, MAY NOT BE OFFERED OR SOLD EXCEPT PURSUANT TO AN EFFECTIVE REGIST

Securities Purchase Agreement, dated as of July 14, 2022, by and between the registrant and FirstFire Global Opportunities Fund, LLC.

Exhibit 10.7 SECURITIES PURCHASE AGREEMENT This SECURITIES PURCHASE AGREEMENT (the ?Agreement?), dated as of July 14, 2022, by and between SIMPLICITY ESPORTS AND GAMING COMPANY, a Delaware corporation, with headquarters located at 7000 West Palmetto Park Road, Suite 505, Boca Raton, Florida 33433 (the ?Company?), and FirstFire Global Opportunities Fund, LLC (the ?Buyer?). WHEREAS: A. The Company a

Entry into a Material Definitive Agreement, Creation of a Direct Financial Obligation or an Obligation under an Off-Balance Sheet Arrangement of a Registrant, Financial Statements and Exhibits

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (date of earliest event reported): July 14, 2022 SIMPLICITY ESPORTS AND GAMING COMPANY (Exact name of registrant as specified in its charter) Delaware 001-38188 82-1231127 (State or other jurisdiction of incorporation)

Letter from Prager Metis CPAs LLP, dated July 21, 2022, addressed to the Securities and Exchange Commission.

Exhibit 16.1 July 21, 2022 Securities and Exchange Commission 100 F Street N.E. Washington, D.C. 20549 Dear Sirs/Madams: We have read Item 4.01 of Form 8-K of Simplicity Esports and Gaming Company dated July 21, 2022. We agree with the statements made concerning our firm contained therein. We have no basis to agree or disagree with other statements of the registrant contained therein. Yours very t

Convertible Promissory Note, dated as of July 14, 2022, issued by the registrant in favor of Jefferson Street Capital, LLC.

Exhibit 10.5 NEITHER THE ISSUANCE AND SALE OF THE SECURITIES REPRESENTED BY THIS CERTIFICATE NOR THE SECURITIES INTO WHICH THESE SECURITIES ARE CONVERTIBLE HAVE BEEN REGISTERED UNDER THE SECURITIES ACT OF 1933, AS AMENDED, OR APPLICABLE STATE SECURITIES LAWS. THE SECURITIES MAY NOT BE OFFERED FOR SALE, SOLD, TRANSFERRED OR ASSIGNED (I) IN THE ABSENCE OF (A) AN EFFECTIVE REGISTRATION STATEMENT FOR

Convertible Promissory Note, dated as of July 14, 2022, issued by the registrant in favor of Ionic Ventures, LLC.

Exhibit 10.2 NEITHER THE ISSUANCE AND SALE OF THE SECURITIES REPRESENTED BY THIS CERTIFICATE NOR THE SECURITIES INTO WHICH THESE SECURITIES ARE CONVERTIBLE HAVE BEEN REGISTERED UNDER THE SECURITIES ACT OF 1933, AS AMENDED, OR APPLICABLE STATE SECURITIES LAWS. THE SECURITIES MAY NOT BE OFFERED FOR SALE, SOLD, TRANSFERRED OR ASSIGNED (I) IN THE ABSENCE OF (A) AN EFFECTIVE REGISTRATION STATEMENT FOR

Securities Purchase Agreement, dated as of July 14, 2022, by and between the registrant and Ionic Ventures, LLC.

Exhibit 10.1 SECURITIES PURCHASE AGREEMENT This SECURITIES PURCHASE AGREEMENT (the ?Agreement?), dated as of July 14, 2022, by and between SIMPLICITY ESPORTS AND GAMING COMPANY, a Delaware corporation, with headquarters located at 7000 West Palmetto Park Road, Suite 505, Boca Raton, Florida 33433 (the ?Company?), and Ionic Ventures, LLC, (the ?Buyer?). WHEREAS: A. The Company and the Buyer are exe

Securities Purchase Agreement, dated as of July 14, 2022, by and between the registrant and GS Capital Partners, LLC.

Exhibit 10.10 SECURITIES PURCHASE AGREEMENT This SECURITIES PURCHASE AGREEMENT (the ?Agreement?), dated as of July 14, 2022, by and between SIMPLICITY ESPORTS AND GAMING COMPANY, a Delaware corporation, with headquarters located at 7000 West Palmetto Park Road, Suite 505, Boca Raton, Florida 33433 (the ?Company?), and GS Capital Partners, LLC (the ?Buyer?). WHEREAS: A. The Company and the Buyer ar

Convertible Promissory Note, dated as of July 14, 2022, issued by the registrant in favor of GS Capital Partners, LLC.

EX-10.11 12 ex10-11.htm Exhibit 10.11 NEITHER THE ISSUANCE AND SALE OF THE SECURITIES REPRESENTED BY THIS CERTIFICATE NOR THE SECURITIES INTO WHICH THESE SECURITIES ARE CONVERTIBLE HAVE BEEN REGISTERED UNDER THE SECURITIES ACT OF 1933, AS AMENDED, OR APPLICABLE STATE SECURITIES LAWS. THE SECURITIES MAY NOT BE OFFERED FOR SALE, SOLD, TRANSFERRED OR ASSIGNED (I) IN THE ABSENCE OF (A) AN EFFECTIVE RE

Common Stock Purchase Warrant, dated as of July 14, 2022, issued by the registrant in favor of GS Capital Partners, LLC.

Exhibit 10.12 NEITHER THIS SECURITY NOR THE SECURITIES FOR WHICH THIS SECURITY IS EXERCISABLE HAVE BEEN REGISTERED WITH THE SECURITIES AND EXCHANGE COMMISSION OR THE SECURITIES COMMISSION OF ANY STATE IN RELIANCE UPON AN EXEMPTION FROM REGISTRATION UNDER THE SECURITIES ACT OF 1933, AS AMENDED (THE ?SECURITIES ACT?), AND, ACCORDINGLY, MAY NOT BE OFFERED OR SOLD EXCEPT PURSUANT TO AN EFFECTIVE REGIS

Convertible Promissory Note, dated as of July 14, 2022, issued by the registrant in favor of FirstFire Global Opportunities Fund, LLC.

Exhibit 10.8 NEITHER THE ISSUANCE AND SALE OF THE SECURITIES REPRESENTED BY THIS CERTIFICATE NOR THE SECURITIES INTO WHICH THESE SECURITIES ARE CONVERTIBLE HAVE BEEN REGISTERED UNDER THE SECURITIES ACT OF 1933, AS AMENDED, OR APPLICABLE STATE SECURITIES LAWS. THE SECURITIES MAY NOT BE OFFERED FOR SALE, SOLD, TRANSFERRED OR ASSIGNED (I) IN THE ABSENCE OF (A) AN EFFECTIVE REGISTRATION STATEMENT FOR

Securities Purchase Agreement, dated as of July 14, 2022, by and between the registrant and Jefferson Street Capital, LLC.

Exhibit 10.4 SECURITIES PURCHASE AGREEMENT This SECURITIES PURCHASE AGREEMENT (the ?Agreement?), dated as of July 14, 2022, by and between SIMPLICITY ESPORTS AND GAMING COMPANY, a Delaware corporation, with headquarters located at 7000 West Palmetto Park Road, Suite 505, Boca Raton, Florida 33433 (the ?Company?), and Jefferson Street Capital, LLC, (the ?Buyer?). WHEREAS: A. The Company and the Buy

Changes in Registrant's Certifying Accountant, Financial Statements and Exhibits

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (date of earliest event reported): July 7, 2022 SIMPLICITY ESPORTS AND GAMING COMPANY (Exact name of registrant as specified in its charter) Delaware 001-38188 82-1231127 (State or other jurisdiction of incorporation)

Common Stock Purchase Warrant, dated as of July 14, 2022, issued by the registrant in favor of Ionic Ventures, LLC.

Exhibit 10.3 NEITHER THIS SECURITY NOR THE SECURITIES FOR WHICH THIS SECURITY IS EXERCISABLE HAVE BEEN REGISTERED WITH THE SECURITIES AND EXCHANGE COMMISSION OR THE SECURITIES COMMISSION OF ANY STATE IN RELIANCE UPON AN EXEMPTION FROM REGISTRATION UNDER THE SECURITIES ACT OF 1933, AS AMENDED (THE ?SECURITIES ACT?), AND, ACCORDINGLY, MAY NOT BE OFFERED OR SOLD EXCEPT PURSUANT TO AN EFFECTIVE REGIST

Common Stock Purchase Warrant, dated as of July 14, 2022, issued by the registrant in favor of Jefferson Street Capital, LLC.

Exhibit 10.6 NEITHER THIS SECURITY NOR THE SECURITIES FOR WHICH THIS SECURITY IS EXERCISABLE HAVE BEEN REGISTERED WITH THE SECURITIES AND EXCHANGE COMMISSION OR THE SECURITIES COMMISSION OF ANY STATE IN RELIANCE UPON AN EXEMPTION FROM REGISTRATION UNDER THE SECURITIES ACT OF 1933, AS AMENDED (THE ?SECURITIES ACT?), AND, ACCORDINGLY, MAY NOT BE OFFERED OR SOLD EXCEPT PURSUANT TO AN EFFECTIVE REGIST

SIMPLICITY ESPORTS AND GAMING COMPANY 7000 W. Palmetto Park Rd., Suite 505 Boca Raton, FL 33433 July 22, 2022

SIMPLICITY ESPORTS AND GAMING COMPANY 7000 W. Palmetto Park Rd., Suite 505 Boca Raton, FL 33433 July 22, 2022 FILING VIA EDGAR Office of Trade & Services U.S. Securities and Exchange Commission 100 F Street, N.E. Washington, D.C. 20549 Re: Simplicity Esports and Gaming Company Request for Withdrawal of Registration Statement on Form S-1 Filed on April 10, 2020, as amended File No. 333-237634 Ladie

Departure of Directors or Certain Officers; Election of Directors; Appointment of Certain Officers; Compensatory Arrangements of Certain Officers, Other Events

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (date of earliest event reported): June 23, 2022 SIMPLICITY ESPORTS AND GAMING COMPANY (Exact name of registrant as specified in its charter) Delaware 001-38188 82-1231127 (State or other jurisdiction of incorporation)

SIMPLICITY ESPORTS AND GAMING COMPANY 11,897,214 Shares of Common Stock Underlying Convertible Promissory Notes 2,267,897 Shares of Common Stock Underlying Warrants 36,874 Shares of Common Stock for Resale by Selling Securityholders

Filed Pursuant to Rule 424(b)(3) Registration No. 333-265521 SIMPLICITY ESPORTS AND GAMING COMPANY 11,897,214 Shares of Common Stock Underlying Convertible Promissory Notes 2,267,897 Shares of Common Stock Underlying Warrants 36,874 Shares of Common Stock for Resale by Selling Securityholders This prospectus relates to the issuance by us of up to 11,897,214 shares of our common stock, par value $0

EFFECT

X0101 EFFECT 33 LIVE 2022-06-24 12:00:00 S-1 0001708410 SIMPLICITY ESPORTS & GAMING Co 333-265521

SIMPLICITY ESPORTS AND GAMING COMPANY 7000 W. Palmetto Park Rd., Suite 505 Boca Raton, FL 33433 June 22, 2022

SIMPLICITY ESPORTS AND GAMING COMPANY 7000 W. Palmetto Park Rd., Suite 505 Boca Raton, FL 33433 June 22, 2022 CORRESPONDENCE FILING VIA EDGAR Alyssa Wall Office of Trade & Services Division of Corporation Finance U.S. Securities and Exchange Commission 100 F Street, N.E. Washington, D.C. 20549 Re: Simplicity Esports and Gaming Company Registration Statement on Form S-1 Filed June 10, 2022 (File No

As filed with the Securities and Exchange Commission on June 10, 2022

As filed with the Securities and Exchange Commission on June 10, 2022 Registration No.

Filing Fee Table.*

Exhibit 107 CALCULATION OF REGISTRATION FEE Title of each class of securities to be registered Amount to be registered Proposed maximum offering price per share of common stock Proposed maximum aggregate offering price Amount of registration fee Common Stock, par value $0.

List of Subsidiaries*

EXHIBIT 21.1 List of Subsidiaries of Simplicity Esports and Gaming Company Entity Name Place of Organization Simplicity Esports, LLC * Florida PLAYlive Nation, Inc * Delaware PLAYlive Nation Holdings, LLC * Delaware Simplicity One Brasil Ltda ** Brazil Simplicity Happy Valley, LLC *** Oregon Simplicity Redmond, LLC *** Washington Simplicity El Paso, LLC**** Texas Simplicity Union Gap, LLC * Washin

SIMPLICITY ESPORTS AND GAMING COMPANY 7000 W. Palmetto Park Rd., Suite 505 Boca Raton, FL 33433 June 2, 2022

SIMPLICITY ESPORTS AND GAMING COMPANY 7000 W. Palmetto Park Rd., Suite 505 Boca Raton, FL 33433 June 2, 2022 FILING VIA EDGAR Office of Trade & Services U.S. Securities and Exchange Commission 100 F Street, N.E. Washington, D.C. 20549 Re: Simplicity Esports and Gaming Company Request for Withdrawal of Post-Effective Amendment No. 1 to Registration Statement on Form S-1 Filed on May 11, 2022 File N

SIMPLICITY ESPORTS AND GAMING COMPANY 7000 W. Palmetto Park Rd., Suite 505 Boca Raton, FL 33433 June 2, 2022

SIMPLICITY ESPORTS AND GAMING COMPANY 7000 W. Palmetto Park Rd., Suite 505 Boca Raton, FL 33433 June 2, 2022 FILING VIA EDGAR U.S. Securities and Exchange Commission Division of Corporation Finance 100 F Street, N.E. Washington, D.C. 20549 Attention: Ms. Jennifer Lopez Re: Simplicity Esports and Gaming Company Post-Effective Amendment No. 1 to Registration Statement on Form S-1 Filed May 11, 2022

SIMPLICITY ESPORTS AND GAMING COMPANY 7000 W. Palmetto Park Rd., Suite 505 Boca Raton, FL 33433 May 27, 2022

SIMPLICITY ESPORTS AND GAMING COMPANY 7000 W. Palmetto Park Rd., Suite 505 Boca Raton, FL 33433 May 27, 2022 FILING VIA EDGAR Office of Trade & Services U.S. Securities and Exchange Commission 100 F Street, N.E. Washington, D.C. 20549 Re: Simplicity Esports and Gaming Company Request for Withdrawal of Post-Effective Amendment No. 1 to Registration Statement on Form S-1 Filed on May 11, 2022 File N

Regulation FD Disclosure, Financial Statements and Exhibits

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (date of earliest event reported): May 25, 2022 SIMPLICITY ESPORTS AND GAMING COMPANY (Exact name of registrant as specified in its charter) Delaware 001-38188 82-1231127 (State or other jurisdiction of incorporation)

Management expects to report year-over-year revenue growth in excess of 100%

Exhibit 99.1 Simplicity Esports Management Expects Record Revenue for the Fiscal Year Ending May 31, 2022 Management expects to report year-over-year revenue growth in excess of 100% Boca Raton, Florida ? May 25, 2022 (GLOBE NEWSWIRE) ? Simplicity Esports and Gaming Company (OTCQB:WINR) (?Simplicity Esports?) announces that management expects to report record revenue for the fiscal year ending May

Departure of Directors or Certain Officers; Election of Directors; Appointment of Certain Officers; Compensatory Arrangements of Certain Officers

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (date of earliest event reported): May 18, 2022 SIMPLICITY ESPORTS AND GAMING COMPANY (Exact name of registrant as specified in its charter) Delaware 001-38188 82-1231127 (State or other jurisdiction of incorporation)

SIMPLICITY ESPORTS AND GAMING COMPANY 816,200 Shares of Common Stock Underlying Convertible Promissory Notes 175,000 Shares of Common Stock Underlying Warrants 3,276 Shares of Common Stock for Resale by Selling Securityholders

Filed Pursuant to Rule 424(b)(3) Registration No. 333- 264412 SIMPLICITY ESPORTS AND GAMING COMPANY 816,200 Shares of Common Stock Underlying Convertible Promissory Notes 175,000 Shares of Common Stock Underlying Warrants 3,276 Shares of Common Stock for Resale by Selling Securityholders This prospectus relates to the issuance by us of up to 816,200 shares of our common stock, par value $0.0001 pe

Filing Fee Table.*

Exhibit 107 EX-FILING FEES Calculation of Filing Fee Tables Form S-1 (Form Type) SIMPLICITY ESPORTS AND GAMING COMPANY (Exact Name of Registrant as Specified in its Charter) Table 1: Newly Registered and Carry Forward Securities Security Type Security Class Title Fee Calculation or Carry Forward Rule Amount Registered Proposed Maximum Offering Price Per Unit Maximum Aggregate Offering Price Fee Rate Amount of Registration Fee Fees to Be Paid Fees Previously Paid Equity Common stock, $0.

As filed with the Securities and Exchange Commission on May 11, 2022

As filed with the Securities and Exchange Commission on May 11, 2022 Registration No.

List of Subsidiaries*

EX-21.1 3 ex21-1.htm EXHIBIT 21.1 List of Subsidiaries of Simplicity Esports and Gaming Company Entity Name Place of Organization Simplicity Esports, LLC * Florida PLAYlive Nation, Inc * Delaware PLAYlive Nation Holdings, LLC * Delaware Simplicity One Brasil Ltda ** Brazil Simplicity Happy Valley, LLC *** Oregon Simplicity Redmond, LLC *** Washington Simplicity El Paso, LLC**** Texas Simplicity Un

SIMPLICITY ESPORTS AND GAMING COMPANY 7000 W. Palmetto Park Rd., Suite 505 Boca Raton, FL 33433 May 10, 2022

SIMPLICITY ESPORTS AND GAMING COMPANY 7000 W. Palmetto Park Rd., Suite 505 Boca Raton, FL 33433 May 10, 2022 CORRESPONDENCE FILING VIA EDGAR Janice Adeloye Dietrich King Office of Trade & Services U.S. Securities and Exchange Commission 100 F Street, N.E. Washington, D.C. 20549 Re: Simplicity Esports and Gaming Company Registration Statement Filed on Form S-1 Filed on April 21, 2022 (File No. 333-

Mrs. Tarka brings a wealth of public company corporate governance knowledge, technology, and big data experience to Simplicity Esports.

Exhibit 99.1 Simplicity Esports Appoints Former Travelzoo Director Beatrice Tarka as Chairperson Mrs. Tarka brings a wealth of public company corporate governance knowledge, technology, and big data experience to Simplicity Esports. Boca Raton, Florida ? April 29, 2022 (GLOBE NEWSWIRE) ? The Board of Directors of Simplicity Esports and Gaming Company (OTCQB:WINR) (?Simplicity Esports?) has appoint

Regulation FD Disclosure, Financial Statements and Exhibits

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (date of earliest event reported): April 29, 2022 SIMPLICITY ESPORTS AND GAMING COMPANY (Exact name of registrant as specified in its charter) Delaware 001-38188 82-1231127 (State or other jurisdiction of incorporation

Departure of Directors or Certain Officers; Election of Directors; Appointment of Certain Officers; Compensatory Arrangements of Certain Officers

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (date of earliest event reported): April 22, 2022 SIMPLICITY ESPORTS AND GAMING COMPANY (Exact name of registrant as specified in its charter) Delaware 001-38188 82-1231127 (State or other jurisdiction of incorporation

As filed with the Securities and Exchange Commission on April 21, 2022

As filed with the Securities and Exchange Commission on April 21, 2022 Registration No.

Filing Fee Table.*

Exhibit 107 CALCULATION OF REGISTRATION FEE Title of each class of securities to be registered Amount to be registered Proposed maximum offering price per share of common stock Proposed maximum aggregate offering price Amount of registration fee Common Stock, par value $0.

List of Subsidiaries*

EX-21.1 3 ex21-1.htm EXHIBIT 21.1 List of Subsidiaries of Simplicity Esports and Gaming Company Entity Name Place of Organization Simplicity Esports, LLC * Florida PLAYlive Nation, Inc * Delaware PLAYlive Nation Holdings, LLC * Delaware Simplicity One Brasil Ltda ** Brazil Simplicity Happy Valley, LLC *** Oregon Simplicity Redmond, LLC *** Washington Simplicity El Paso, LLC**** Texas Simplicity Un

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q ☒ QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended February 28, 2022 ☐ TRANSITION REPORT PURSUANT

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q ? QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended February 28, 2022 or ? TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission File Number: 001-38188 SIMPLICITY ESPORT

Convertible Promissory Note, dated March 21, 2022 by the Company in favor of GS Capital Partners, LLC. (42)

Exhibit 10.97 NEITHER THE ISSUANCE AND SALE OF THE SECURITIES REPRESENTED BY THIS CERTIFICATE NOR THE SECURITIES INTO WHICH THESE SECURITIES ARE CONVERTIBLE HAVE BEEN REGISTERED UNDER THE SECURITIES ACT OF 1933, AS AMENDED, OR APPLICABLE STATE SECURITIES LAWS. THE SECURITIES MAY NOT BE OFFERED FOR SALE, SOLD, TRANSFERRED OR ASSIGNED (I) IN THE ABSENCE OF (A) AN EFFECTIVE REGISTRATION STATEMENT FOR

Convertible Promissory Note, dated March 21, 2022 by the Company in favor of FirstFire Global Opportunities Fund. (42)

Exhibit 10.93 NEITHER THE ISSUANCE AND SALE OF THE SECURITIES REPRESENTED BY THIS CERTIFICATE NOR THE SECURITIES INTO WHICH THESE SECURITIES ARE CONVERTIBLE HAVE BEEN REGISTERED UNDER THE SECURITIES ACT OF 1933, AS AMENDED, OR APPLICABLE STATE SECURITIES LAWS. THE SECURITIES MAY NOT BE OFFERED FOR SALE, SOLD, TRANSFERRED OR ASSIGNED (I) IN THE ABSENCE OF (A) AN EFFECTIVE REGISTRATION STATEMENT FOR

Securities Purchase Agreement, dated March 21, 2022, by and between the Company and GS Capital Partners, LLC. (42)

Exhibit 10.96 SECURITIES PURCHASE AGREEMENT This SECURITIES PURCHASE AGREEMENT (the ?Agreement?), dated as of March 2 1, 2022, by and between SIMPLICITY ESPORTS AND GAMING COMPANY, a Delaware corporation, with headquarters located at 7000 West Palmetto Park Road, Suite 505, Boca Raton, Florida 33433 (the ?Company?), and GS CAPITAL PARTNERS, LLC (the ?Buyer?). WHEREAS: A. The Company and the Buyer

As filed with the Securities and Exchange Commission on April 7, 2022

As filed with the Securities and Exchange Commission on April 7, 2022 Registration No.

Common Stock Purchase Warrant, dated as of March 21, 2022, to FirstFire Global Opportunities Fund LLC. (42)

Exhibit 10.94 NEITHER THIS SECURITY NOR THE SECURITIES FOR WHICH THIS SECURITY IS EXERCISABLE HAVE BEEN REGISTERED WITH THE SECURITIES AND EXCHANGE COMMISSION OR THE SECURITIES COMMISSION OF ANY STATE IN RELIANCE UPON AN EXEMPTION FROM REGISTRATION UNDER THE SECURITIES ACT OF 1933, AS AMENDED (THE ?SECURITIES ACT?), AND, ACCORDINGLY, MAY NOT BE OFFERED OR SOLD EXCEPT PURSUANT TO AN EFFECTIVE REGIS

List of Subsidiaries*

EXHIBIT 21.1 List of Subsidiaries of Simplicity Esports and Gaming Company Entity Name Place of Organization Simplicity Esports, LLC * Florida PLAYlive Nation, Inc * Delaware PLAYlive Nation Holdings, LLC * Delaware Simplicity One Brasil Ltda ** Brazil Simplicity Happy Valley, LLC *** Oregon Simplicity Redmond, LLC *** Washington Simplicity El Paso, LLC**** Texas Simplicity Union Gap, LLC * Washin

Amendment and Waiver Pursuant to Convertible Promissory Note dated March 16, 2022, by and between the Company and LGH Investments, LLC. (42)

EX-10.101 20 ex10-101.htm Exhibit 10.101 Amendment and Waiver Pursuant to Convertible Promissory Note Dated as of March 16, 2022 This Amendment and Waiver Pursuant to Convertible Promissory Note (this “Amendment”), dated as of the date first set forth above (the “Amendment Date”), is entered into by and between Simplicity Esports and Gaming Company, a Delaware corporation (the “Company”) and LGH I

Registration Rights Agreement, dated March 21, 2022, by and between the Company and FirstFire Global Opportunities Fund LLC. (42)

Exhibit 10.95 REGISTRATION RIGHTS AGREEMENT This Registration Rights Agreement (this ?Agreement?) is made and entered into as of March 21, 2022 between Simplicity Esports and Gaming Company, a Delaware corporation (the ?Company?), and FIRSTFIRE GLOBAL OPPORTUNITIES FUND, LLC (?Holder?). This Agreement is made pursuant to the Securities Purchase Agreement, dated as of the date hereof, between the C

Amendment No. 2 to Promissory Note and Securities Purchase Agreement dated March 16, 2022, by and between the Company and Labrys Fund, LP. (42)

Exhibit 10.100 AMENDMENT #2 TO THE PROMISSORY NOTE AND SECURITIES PURCHASE AGREEMENT DATED FEBRUARY 19, 2021 Dated as of March 16, 2022 This AMENDMENT #2 (this ?Amendment?) to the Note (as defined below), is entered into on March 16, 2022 (the ?Effective Date?), is entered into by and between Simplicity Esports and Gaming Company, a Delaware corporation (the ?Company?) and Labrys Fund, LP, a Delaw

Convertible Promissory Note, dated March 21, 2022 by the Company in favor of Ionic Ventures, LLC. (42)

Exhibit 10.89 NEITHER THE ISSUANCE AND SALE OF THE SECURITIES REPRESENTED BY THIS CERTIFICATE NOR THE SECURITIES INTO WHICH THESE SECURITIES ARE CONVERTIBLE HAVE BEEN REGISTERED UNDER THE SECURITIES ACT OF 1933, AS AMENDED, OR APPLICABLE STATE SECURITIES LAWS. THE SECURITIES MAY NOT BE OFFERED FOR SALE, SOLD, TRANSFERRED OR ASSIGNED (I) IN THE ABSENCE OF (A) AN EFFECTIVE REGISTRATION STATEMENT FOR

Common Stock Purchase Warrant, dated as of March 21, 2022, to Ionic Ventures, LLC. (42)

Exhibit 10.90 NEITHER THIS SECURITY NOR THE SECURITIES FOR WHICH THIS SECURITY IS EXERCISABLE HAVE BEEN REGISTERED WITH THE SECURITIES AND EXCHANGE COMMISSION OR THE SECURITIES COMMISSION OF ANY STATE IN RELIANCE UPON AN EXEMPTION FROM REGISTRATION UNDER THE SECURITIES ACT OF 1933, AS AMENDED (THE ?SECURITIES ACT?), AND, ACCORDINGLY, MAY NOT BE OFFERED OR SOLD EXCEPT PURSUANT TO AN EFFECTIVE REGIS

Securities Purchase Agreement, dated March 21, 2022, by and between the Company and FirstFire Global Opportunities Fund LLC. (42)

Exhibit 10.92 SECURITIES PURCHASE AGREEMENT This SECURITIES PURCHASE AGREEMENT (the ?Agreement?), dated as of March 2 1, 2022, by and between SIMPLICITY ESPORTS AND GAMING COMPANY, a Delaware corporation, with headquarters located at 7000 West Palmetto Park Road, Suite 505, Boca Raton, Florida 33433 (the ?Company?), and FIRSTFIRE GLOBAL OPPORTUNITIES FUND, LLC (the ?Buyer?). WHEREAS: A. The Compan

Common Stock Purchase Warrant, dated as of March 21, 2022, to GS Capital Partners, LLC. (42)

Exhibit 10.98 NEITHER THIS SECURITY NOR THE SECURITIES FOR WHICH THIS SECURITY IS EXERCISABLE HAVE BEEN REGISTERED WITH THE SECURITIES AND EXCHANGE COMMISSION OR THE SECURITIES COMMISSION OF ANY STATE IN RELIANCE UPON AN EXEMPTION FROM REGISTRATION UNDER THE SECURITIES ACT OF 1933, AS AMENDED (THE ?SECURITIES ACT?), AND, ACCORDINGLY, MAY NOT BE OFFERED OR SOLD EXCEPT PURSUANT TO AN EFFECTIVE REGIS

Securities Purchase Agreement, dated March 21, 2022, by and between the Company and Ionic Ventures, LLC. (42)

Exhibit 10.88 SECURITIES PURCHASE AGREEMENT This SECURITIES PURCHASE AGREEMENT (the ?Agreement?), dated as of March 2 1, 2022, by and between SIMPLICITY ESPORTS AND GAMING COMPANY, a Delaware corporation, with headquarters located at 7000 West Palmetto Park Road, Suite 505, Boca Raton, Florida 33433 (the ?Company?), and Ionic Ventures, LLC (the ?Buyer?). WHEREAS: A. The Company and the Buyer are e

Registration Rights Agreement, dated March 21, 2022, by and between the Company and Ionic Ventures, LLC. (42)

EX-10.91 10 ex10-91.htm Exhibit 10.91 REGISTRATION RIGHTS AGREEMENT This Registration Rights Agreement (this “Agreement”) is made and entered into as of March 21, 2022 between Simplicity Esports and Gaming Company, a Delaware corporation (the “Company”), and Ionic Ventures, LLC (“Holder”). This Agreement is made pursuant to the Securities Purchase Agreement, dated as of the date hereof, between th

Amendment and Waiver Pursuant to Convertible Promissory Note dated March 16, 2022, by and between the Company and Lucas Ventures, LLC. (42)

Exhibit 10.102 Amendment and Waiver Pursuant to Convertible Promissory Note Dated as of March 16, 2022 This Amendment and Waiver Pursuant to Convertible Promissory Note (this ?Amendment?), dated as of the date first set forth above (the ?Amendment Date?), is entered into by and between Simplicity Esports and Gaming Company, a Delaware corporation (the ?Company?) and Lucas Ventures, LLC, an Arizona

Registration Rights Agreement, dated March 21, 2022, by and between the Company and GS Capital Partners, LLC. (42)

Exhibit 10.99 REGISTRATION RIGHTS AGREEMENT This Registration Rights Agreement (this ?Agreement?) is made and entered into as of March 21, 2022 between Simplicity Esports and Gaming Company, a Delaware corporation (the ?Company?), and GS CAPITAL PARTNERS, LLC (?Holder?). This Agreement is made pursuant to the Securities Purchase Agreement, dated as of the date hereof, between the Company and Holde

Calculation of Registration Fee.*

Exhibit 107 CALCULATION OF REGISTRATION FEE Title of Each Class of Securities to be Registered Proposed Maximum Aggregate Offering Price(1) Amount of Registration Fee Units(2) $ 11,500,000 $ 1,493 Common stock, par value $0.

Common Stock Purchase Warrant dated as of April 1, 2022, issued by the registrant in favor of Jefferson Street Capital LLC.(41)

Exhibit 10.3 NEITHER THIS SECURITY NOR THE SECURITIES FOR WHICH THIS SECURITY IS EXERCISABLE HAVE BEEN REGISTERED WITH THE SECURITIES AND EXCHANGE COMMISSION OR THE SECURITIES COMMISSION OF ANY STATE IN RELIANCE UPON AN EXEMPTION FROM REGISTRATION UNDER THE SECURITIES ACT OF 1933, AS AMENDED (THE ?SECURITIES ACT?), AND, ACCORDINGLY, MAY NOT BE OFFERED OR SOLD EXCEPT PURSUANT TO AN EFFECTIVE REGIST

Securities Purchase Agreement, dated as of April 1, 2022, by and between the registrant and Jefferson Street Capital LLC.(41)

Exhibit 10.1 SECURITIES PURCHASE AGREEMENT This SECURITIES PURCHASE AGREEMENT (the ?Agreement?), dated as of April 1, 2022, by and between SIMPLICITY ESPORTS AND GAMING COMPANY, a Delaware corporation, with headquarters located at 7000 West Palmetto Park Road, Suite 505, Boca Raton, Florida 33433 (the ?Company?), and Jefferson Street Capital LLC, a New Jersey limited liability company with an addr

Entry into a Material Definitive Agreement, Creation of a Direct Financial Obligation or an Obligation under an Off-Balance Sheet Arrangement of a Registrant, Financial Statements and Exhibits

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (date of earliest event reported): April 1, 2022 SIMPLICITY ESPORTS AND GAMING COMPANY (Exact name of registrant as specified in its charter) Delaware 001-38188 82-1231127 (State or other jurisdiction of incorporation)

Registration Rights Agreement, dated as of April 1, 2022, by and between the registrant and Jefferson Street Capital LLC.(41)

Exhibit 10.4 REGISTRATION RIGHTS AGREEMENT This Registration Rights Agreement (this ?Agreement?) is made and entered into as of April 1, 2022 between Simplicity Esports and Gaming Company, a Delaware corporation (the ?Company?), and Jefferson Street Capital LLC (?Holder?). This Agreement is made pursuant to the Securities Purchase Agreement, dated as of the date hereof, between the Company and Hol

Convertible Promissory Note, dated as of April 1, 2022, issued by the registrant in favor of Jefferson Street Capital LLC.(41)

Exhibit 10.2 NEITHER THE ISSUANCE AND SALE OF THE SECURITIES REPRESENTED BY THIS CERTIFICATE NOR THE SECURITIES INTO WHICH THESE SECURITIES ARE CONVERTIBLE HAVE BEEN REGISTERED UNDER THE SECURITIES ACT OF 1933, AS AMENDED, OR APPLICABLE STATE SECURITIES LAWS. THE SECURITIES MAY NOT BE OFFERED FOR SALE, SOLD, TRANSFERRED OR ASSIGNED (I) IN THE ABSENCE OF (A) AN EFFECTIVE REGISTRATION STATEMENT FOR

Entry into a Material Definitive Agreement, Creation of a Direct Financial Obligation or an Obligation under an Off-Balance Sheet Arrangement of a Registrant

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (date of earliest event reported): March 16, 2022 SIMPLICITY ESPORTS AND GAMING COMPANY (Exact name of registrant as specified in its charter) Delaware 001-38188 82-1231127 (State or other jurisdiction of incorporation

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q ☒ QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended November 30, 2021 ☐ TRANSITION REPORT PURSUANT

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q ? QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended November 30, 2021 or ? TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission File Number: 001-38188 SIMPLICITY ESPORT

List of Subsidiaries*

EXHIBIT 21.1 List of Subsidiaries of Simplicity Esports and Gaming Company Entity Name Place of Organization Simplicity Esports, LLC * Florida PLAYlive Nation, Inc * Delaware PLAYlive Nation Holdings, LLC * Delaware Simplicity One Brasil Ltda ** Brazil Simplicity Happy Valley, LLC *** Oregon Simplicity Redmond, LLC *** Washington Simplicity El Paso, LLC**** Texas Simplicity Union Gap, LLC * Washin

As filed with the Securities and Exchange Commission on January 10, 2022

As filed with the Securities and Exchange Commission on January 10, 2022 Registration No.

WINR / Simplicity Esports and Gaming Co / AQR CAPITAL MANAGEMENT LLC - AQR CAPITAL MANAGEMENT LLC Passive Investment

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13G Under the Securities Exchange Act of 1934 (Amendment No. 1)* SIMPLICITY ESPORTS AND GAMING COMPANY (Name of Issuer) Common Stock - $0.0001 par value (Title of Class of Securities) 82887P209 (CUSIP Number) December 20, 2021 (Date of Event which Requires Filing of this Statement) Check the appropriate box to designa

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q/A (Amendment No. 1) ☒ QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended August 31, 2021 ☐ TRANSITIO

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q/A (Amendment No. 1) ? QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended August 31, 2021 or ? TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission File Number: 001-38188

SIMPLICITY ESPORTS AND GAMING COMPANY 806,126 Shares of Common Stock Underlying Warrants 775,496 Shares of Common Stock for Resale by Selling Securityholders 32,688 Warrants to Purchase Common Stock for Resale by Selling Securityholders

PROSPECTUS Filed Pursuant to Rule 424(b)(3) Registration No. 333-228906 SIMPLICITY ESPORTS AND GAMING COMPANY 806,126 Shares of Common Stock Underlying Warrants 775,496 Shares of Common Stock for Resale by Selling Securityholders 32,688 Warrants to Purchase Common Stock for Resale by Selling Securityholders This prospectus relates to the issuance by us of up to 806,126 shares of our common stock,

As filed with the Securities and Exchange Commission on November 16, 2021

As filed with the Securities and Exchange Commission on November 16, 2021 Registration No.

Submission of Matters to a Vote of Security Holders

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (date of earliest event reported): October 21, 2021 SIMPLICITY ESPORTS AND GAMING COMPANY (Exact name of registrant as specified in its charter) Delaware 001-38188 82-1231127 (State or other jurisdiction of incorporati

SIMPLICITY ESPORTS AND GAMING COMPANY 609,888 Shares of Common Stock Underlying Convertible Promissory Notes 2,267,897 Shares of Common Stock Underlying Warrants 69,852 Shares of Common Stock for Resale by Selling Securityholders

Filed Pursuant to Rule 424(b)(3) Registration No. 333-259993 SIMPLICITY ESPORTS AND GAMING COMPANY 609,888 Shares of Common Stock Underlying Convertible Promissory Notes 2,267,897 Shares of Common Stock Underlying Warrants 69,852 Shares of Common Stock for Resale by Selling Securityholders This prospectus relates to the issuance by us of up to 609,888 shares of our common stock, par value $0.0001

Certificate of Amendment to Third Amended and Restated Certificate of Incorporation, as amended, filed with Delaware Secretary of State on September 18, 2020.

Exhibit 3.2 STATE OF DELAWARE CERTIFICATE OF AMENDMENT TO THIRD AMENDED AND RESTATED CERTIFICATE OF INCORPORATION, AS AMENDED, OF SIMPLICITY ESPORTS AND GAMING COMPANY Under Section 242 of the Delaware General Corporation Law Simplicity Esports and Gaming Company, a corporation organized and existing under and by virtue of the General Corporation Law of the State of Delaware (the ?Corporation?), d

Form of Underwriting Agreement*

EXHIBIT 1.1 UNITS EACH UNIT CONSISTING OF ONE SHARE of Common Stock and ONE Warrant TO PURCHASE ONE SHARE OF COMMON STOCK SIMPLICITY ESPORTS AND GAMING COMPANY UNDERWRITING AGREEMENT , 2021 Maxim Group LLC Investment Banking 405 Lexington Avenue, 2nd Fl. New York, New York 10174 As Representative of the Several Underwriters, if any, named in Schedule I hereto Ladies and Gentlemen: The undersigned,

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q ☒ QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended August 31, 2021 ☐ TRANSITION REPORT PURSUANT TO

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q ? QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended August 31, 2021 or ? TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission File Number: 001-38188 SIMPLICITY ESPORTS

List of Subsidiaries*

EXHIBIT 21.1 List of Subsidiaries of Simplicity Esports and Gaming Company Entity Name Place of Organization Simplicity Esports, LLC * Florida PLAYlive Nation, Inc * Delaware PLAYlive Nation Holdings, LLC * Delaware Simplicity One Brasil Ltda ** Brazil Simplicity Happy Valley, LLC *** Oregon Simplicity Redmond, LLC *** Washington Simplicity El Paso, LLC**** Texas Simplicity Union Gap, LLC * Washin

Amendment No. 1 to Convertible Promissory Note, dated September 17, 2021, between the Company and FirstFire Global Opportunities Fund LLC (40)

EXHIBIT 10.80 Amendment No. 1 to Convertible Promissory Note Dated as of September 17, 2021 This Amendment No. 1 to Convertible Promissory Note (this ?Amendment?), dated as of the date first set forth above, is entered into by and between Simplicity Esports and Gaming Company, a Delaware corporation (the ?Company?) and FIRSTFIRE GLOBAL OPPORTUNITIES FUND, LLC, a Delaware limited liability company

As filed with the Securities and Exchange Commission on October 12, 2021

As filed with the Securities and Exchange Commission on October 12, 2021 Registration No.

SIMPLICITY ESPORTS AND GAMING COMPANY 7000 W. Palmetto Park Rd., Suite 505 Boca Raton, FL 33433 October 7, 2021

SIMPLICITY ESPORTS AND GAMING COMPANY 7000 W. Palmetto Park Rd., Suite 505 Boca Raton, FL 33433 October 7, 2021 CORRESPONDENCE FILING VIA EDGAR Mr. Donald Field Office of Trade & Services U.S. Securities and Exchange Commission 100 F Street, N.E. Washington, D.C. 20549 Re: Simplicity Esports and Gaming Company Registration Statement Filed on Form S-1 (File No. 333-259993) Dear Mr. Field: On behalf

Registration Rights Agreement, dated as of September 28, 2021, by and between the registrant and Ionic Ventures, LLC.

Exhibit 10.4 REGISTRATION RIGHTS AGREEMENT This Registration Rights Agreement (this ?Agreement?) is made and entered into as of September 28, 2021 between Simplicity Esports and Gaming Company, a Delaware corporation (the ?Company?), and Ionic Ventures, LLC (?Holder?). This Agreement is made pursuant to the Securities Purchase Agreement, dated as of the date hereof, between the Company and Holder

Power of Attorney (43)

As filed with the Securities and Exchange Commission on October 1, 2021 Registration No.

Amendment No. 2 to Convertible Promissory Note, dated October 1, 2021, between the Company and FirstFire Global Opportunities Fund LLC (39)

Exhibit 10.82 Amendment No. 2 to Convertible Promissory Note Dated as of October 1, 2021 This Amendment No. 2 to Convertible Promissory Note (this ?Amendment?), dated as of the date first set forth above, is entered into by and between Simplicity Esports and Gaming Company, a Delaware corporation (the ?Company?) and FIRSTFIRE GLOBAL OPPORTUNITIES FUND, LLC, a Delaware limited liability company (?H

List of Subsidiaries*

EXHIBIT 21.1 List of Subsidiaries of Simplicity Esports and Gaming Company Entity Name Place of Organization Simplicity Esports, LLC * Florida PLAYlive Nation, Inc * Delaware PLAYlive Nation Holdings, LLC * Delaware Simplicity One Brasil Ltda ** Brazil Simplicity Happy Valley, LLC *** Oregon Simplicity Redmond, LLC *** Washington Simplicity El Paso, LLC**** Texas Simplicity Union Gap, LLC * Washin

Amendment No. 1 to Common Stock Purchase Warrant, dated as of September 9, 2021, between the Company and GS Capital Partners, LLC (39)

Exhibit 10.85 Amendment No. 1 to Common Stock Purchase Warrant Dated as of September 9, 2021 This Amendment No. 1 to Common Stock Purchase Warrant (this ?Amendment?), dated as of the date first set forth above, is entered into by and between Simplicity Esports and Gaming Company, a Delaware corporation (the ?Company?) and GS CAPITAL PARTNERS, LLC, a Delaware limited liability company (?GS?). The C

Amendment No. 1 to Common Stock Purchase Warrant, dated as of September 9, 2021, between the Company and Jefferson Street Capital, LLC (39)

Exhibit 10.86 Amendment No. 1 to Common Stock Purchase Warrant Dated as of September 9, 2021 This Amendment No. 1 to Common Stock Purchase Warrant (this ?Amendment?), dated as of the date first set forth above, is entered into by and between Simplicity Esports and Gaming Company, a Delaware corporation (the ?Company?) and Jefferson Street Capital LLC, a New Jersey limited liability company (?Holde

Common Stock Purchase Warrant, dated as of October 1, 2021, to FirstFire Global Opportunities Fund LLC (39)

Exhibit 10.83 NEITHER THIS SECURITY NOR THE SECURITIES FOR WHICH THIS SECURITY IS EXERCISABLE HAVE BEEN REGISTERED WITH THE SECURITIES AND EXCHANGE COMMISSION OR THE SECURITIES COMMISSION OF ANY STATE IN RELIANCE UPON AN EXEMPTION FROM REGISTRATION UNDER THE SECURITIES ACT OF 1933, AS AMENDED (THE ?SECURITIES ACT?), AND, ACCORDINGLY, MAY NOT BE OFFERED OR SOLD EXCEPT PURSUANT TO AN EFFECTIVE REGIS

Amendment No. 1 to Common Stock Purchase Warrant, dated as of September 9, 2021, between the Company and Lucas Ventures, LLC (39)

Exhibit 10.87 Amendment No. 1 to Common Stock Purchase Warrant Dated as of September 9, 2021 This Amendment No. 1 to Common Stock Purchase Warrant (this ?Amendment?), dated as of the date first set forth above, is entered into by and between Simplicity Esports and Gaming Company, a Delaware corporation (the ?Company?) and Lucas Ventures, LLC, an Arizona limited liability company (?Holder?). The Co

Amendment No. 1 to Convertible Promissory Note, dated September 17, 2021, between the Company and FirstFire Global Opportunities Fund LLC*

Exhibit 10.80 Amendment No. 1 to Convertible Promissory Note Dated as of September 17, 2021 This Amendment No. 1 to Convertible Promissory Note (this ?Amendment?), dated as of the date first set forth above, is entered into by and between Simplicity Esports and Gaming Company, a Delaware corporation (the ?Company?) and FIRSTFIRE GLOBAL OPPORTUNITIES FUND, LLC, a Delaware limited liability company

Common Stock Purchase Warrant, dated as of September 28, 2021, to Ionic Ventures, LLC (37)

Exhibit 10.3 NEITHER THIS SECURITY NOR THE SECURITIES FOR WHICH THIS SECURITY IS EXERCISABLE HAVE BEEN REGISTERED WITH THE SECURITIES AND EXCHANGE COMMISSION OR THE SECURITIES COMMISSION OF ANY STATE IN RELIANCE UPON AN EXEMPTION FROM REGISTRATION UNDER THE SECURITIES ACT OF 1933, AS AMENDED (THE ?SECURITIES ACT?), AND, ACCORDINGLY, MAY NOT BE OFFERED OR SOLD EXCEPT PURSUANT TO AN EFFECTIVE REGIST

Entry into a Material Definitive Agreement, Creation of a Direct Financial Obligation or an Obligation under an Off-Balance Sheet Arrangement of a Registrant, Financial Statements and Exhibits

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (date of earliest event reported): September 28, 2021 SIMPLICITY ESPORTS AND GAMING COMPANY (Exact name of registrant as specified in its charter) Delaware 001-38188 82-1231127 (State or other jurisdiction of incorpora

Common Stock Purchase Warrant, dated as of September 17, 2021, to FirstFire Global Opportunities Fund LLC (39)

Exhibit 10.81 NEITHER THIS SECURITY NOR THE SECURITIES FOR WHICH THIS SECURITY IS EXERCISABLE HAVE BEEN REGISTERED WITH THE SECURITIES AND EXCHANGE COMMISSION OR THE SECURITIES COMMISSION OF ANY STATE IN RELIANCE UPON AN EXEMPTION FROM REGISTRATION UNDER THE SECURITIES ACT OF 1933, AS AMENDED (THE ?SECURITIES ACT?), AND, ACCORDINGLY, MAY NOT BE OFFERED OR SOLD EXCEPT PURSUANT TO AN EFFECTIVE REGIS

Convertible Promissory Note, dated September 28, 2021, by the Company in favor of Ionic Ventures, LLC (37)

Exhibit 10.2 NEITHER THE ISSUANCE AND SALE OF THE SECURITIES REPRESENTED BY THIS CERTIFICATE NOR THE SECURITIES INTO WHICH THESE SECURITIES ARE CONVERTIBLE HAVE BEEN REGISTERED UNDER THE SECURITIES ACT OF 1933, AS AMENDED, OR APPLICABLE STATE SECURITIES LAWS. THE SECURITIES MAY NOT BE OFFERED FOR SALE, SOLD, TRANSFERRED OR ASSIGNED (I) IN THE ABSENCE OF (A) AN EFFECTIVE REGISTRATION STATEMENT FOR

Securities Purchase Agreement, dated September 28, 2021, by and between the Company and Ionic Ventures, LLC (37)

Exhibit 10.1 EXECUTION VERSION SECURITIES PURCHASE AGREEMENT This SECURITIES PURCHASE AGREEMENT (the ?Agreement?), dated as of September 28, 2021, by and between SIMPLICITY ESPORTS AND GAMING COMPANY, a Delaware corporation, with headquarters located at 7000 West Palmetto Park Road, Suite 505, Boca Raton, Florida 33433 (the ?Company?), and Ionic Ventures, LLC (the ?Buyer?). WHEREAS: A. The Company

Common Stock Purchase Warrant, dated as of June 16, 2021, to GS Capital Partners, LLC. (39)

Exhibit 10.67 NEITHER THIS SECURITY NOR THE SECURITIES FOR WHICH THIS SECURITY IS EXERCISABLE HAVE BEEN REGISTERED WITH THE SECURITIES AND EXCHANGE COMMISSION OR THE SECURITIES COMMISSION OF ANY STATE IN RELIANCE UPON AN EXEMPTION FROM REGISTRATION UNDER THE SECURITIES ACT OF 1933, AS AMENDED (THE ?SECURITIES ACT?), AND, ACCORDINGLY, MAY NOT BE OFFERED OR SOLD EXCEPT PURSUANT TO AN EFFECTIVE REGIS

Amendment No. 1 to Common Stock Purchase Warrant, dated as of September 9, 2021, between the Company and FirstFire Global Opportunities Fund LLC (39)

Exhibit 10.84 Amendment No. 1 to Common Stock Purchase Warrant Dated as of September 9, 2021 This Amendment No. 1 to Common Stock Purchase Warrant (this ?Amendment?), dated as of the date first set forth above, is entered into by and between Simplicity Esports and Gaming Company, a Delaware corporation (the ?Company?) and FIRSTFIRE GLOBAL OPPORTUNITIES FUND, LLC, a Delaware limited liability compa

Common Stock Purchase Warrant, dated as of June 11, 2021, to FirstFire Global Opportunities Fund LLC (39)

Exhibit 10.64 NEITHER THIS SECURITY NOR THE SECURITIES FOR WHICH THIS SECURITY IS EXERCISABLE HAVE BEEN REGISTERED WITH THE SECURITIES AND EXCHANGE COMMISSION OR THE SECURITIES COMMISSION OF ANY STATE IN RELIANCE UPON AN EXEMPTION FROM REGISTRATION UNDER THE SECURITIES ACT OF 1933, AS AMENDED (THE ?SECURITIES ACT?), AND, ACCORDINGLY, MAY NOT BE OFFERED OR SOLD EXCEPT PURSUANT TO AN EFFECTIVE REGIS

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amendment No. )

DEF 14A 1 def14a.htm UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amendment No. ) Filed by the Registrant ☒ Filed by a Party other than the Registrant ☐ Check the appropriate box: ☐ Preliminary Proxy Statement ☐ Confidential, for Use of the Commission Only (as permitted by Rule

Simplicity Esports

Exhibit 99.1 Simplicity Esports Signs Two Year Exclusive Retail Distribution Agreement with Leading Gaming Supplement Company ADVANCED? Simplicity to receive over $500,000 in Retail Outlet Access Fees and become an exclusive retail distributor for ADVANCED?, who recorded 210% year-over-year growth in online, direct to consumer sales as of September 2021. Boca Raton, Florida ? September 9, 2021 (GL

Exclusive Energy Drink Distribution Agreement dated September 8, 2021 between the registrant and Advanced, LLC

Exhibit 10.1 EXCLUSIVE ENERGY DRINK DISTRIBUTION AGREEMENT Dated as of September 8, 2021 This Exclusive Energy Drink Distribution Agreement (this ?Agreement?) is entered into on the date first set forth above (the ?Effective Date?) by and between Advanced, LLC, a Minnesota limited liability company (?Advanced?) and Simplicity Esports and Gaming Inc., a Delaware corporation (?Simplicity?). Advanced

Regulation FD Disclosure, Entry into a Material Definitive Agreement, Financial Statements and Exhibits

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (date of earliest event reported): September 8, 2021 SIMPLICITY ESPORTS AND GAMING COMPANY (Exact name of registrant as specified in its charter) Delaware 001-38188 82-1231127 (State or other jurisdiction of incorporat

Entry into a Material Definitive Agreement, Creation of a Direct Financial Obligation or an Obligation under an Off-Balance Sheet Arrangement of a Registrant, Financial Statements and Exhibits

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (date of earliest event reported): August 31, 2021 SIMPLICITY ESPORTS AND GAMING COMPANY (Exact name of registrant as specified in its charter) Delaware 001-38188 82-1231127 (State or other jurisdiction of incorporatio

Registration Rights Agreement, dated as of August 31, 2021, by and between the registrant and LGH Investments, LLC.

Exhibit 10.7 REGISTRATION RIGHTS AGREEMENT THIS REGISTRATION RIGHTS AGREEMENT (this ?Agreement?), dated as of August 31, 2021, is made by and between Simplicity Esports and Gaming Company, a Delaware corporation (the ?Company?), and LGH Investments, LLC (the ?Holder?). The Company and the Holder are hereinafter sometimes collectively referred to as the ?Parties? and each a ?Party? to this Agreemen

Common Stock Purchase Warrant, dated as of August 31, 2021, to Lucas Ventures, LLC (36)

Exhibit 10.4 NEITHER THIS SECURITY NOR THE SECURITIES FOR WHICH THIS SECURITY IS EXERCISABLE HAVE BEEN REGISTERED WITH THE SECURITIES AND EXCHANGE COMMISSION OR THE SECURITIES COMMISSION OF ANY STATE IN RELIANCE UPON AN EXEMPTION FROM REGISTRATION UNDER THE SECURITIES ACT OF 1933, AS AMENDED (THE ?SECURITIES ACT?), AND, ACCORDINGLY, MAY NOT BE OFFERED OR SOLD EXCEPT PURSUANT TO AN EFFECTIVE REGIST

Securities Purchase Agreement, dated as of August 31, 2021, by and between the registrant and LGH Investments, LLC.

Exhibit 10.5 SECURITIES PURCHASE AGREEMENT This SECURITIES PURCHASE AGREEAMENT (the ?Agreement?), dated as of August 31, 2021, by and between SIMPLICITY ESPORTS AND GAMING COMPANY, a Delaware corporation, with headquarters located at 7000 West Palmetto Park Road, Suite 505, Boca Raton, Florida 33433 (the ?Company?), and LGH INVESTMENTS, LLC, a Wyoming limited liability company (the ?Buyer?). WHERE

Convertible Promissory Note, dated August 31, 2021, by the Company in favor of Lucas Ventures, LLC (36)

Exhibit 10.2 NEITHER THE ISSUANCE AND SALE OF THE SECURITIES REPRESENTED BY THIS CERTIFICATE NOR THE SECURITIES INTO WHICH THESE SECURITIES ARE CONVERTIBLE HAVE BEEN REGISTERED UNDER THE SECURITIES ACT OF 1933, AS AMENDED, OR APPLICABLE STATE SECURITIES LAWS. THE SECURITIES MAY NOT BE OFFERED FOR SALE, SOLD, TRANSFERRED OR ASSIGNED (I) IN THE ABSENCE OF (A) AN EFFECTIVE REGISTRATION STATEMENT FOR

Convertible Promissory Note, dated August 31, 2021, by the Company in favor of LGH Investments, LLC (36)

Exhibit 10.6 NEITHER THE ISSUANCE AND SALE OF THE SECURITIES REPRESENTED BY THIS CERTIFICATE NOR THE SECURITIES INTO WHICH THESE SECURITIES ARE CONVERTIBLE HAVE BEEN REGISTERED UNDER THE SECURITIES ACT OF 1933, AS AMENDED, OR APPLICABLE STATE SECURITIES LAWS. THE SECURITIES MAY NOT BE OFFERED FOR SALE, SOLD, TRANSFERRED OR ASSIGNED (I) IN THE ABSENCE OF (A) AN EFFECTIVE REGISTRATION STATEMENT FOR

Securities Purchase Agreement, dated August 31, 2021, by and between the Company and Lucas Ventures, LLC (36)

Exhibit 10.1 SECURITIES PURCHASE AGREEMENT This SECURITIES PURCHASE AGREEMENT (the ?Agreement?), dated as of August 31, 2021, by and between SIMPLICITY ESPORTS AND GAMING COMPANY, a Delaware corporation, with headquarters located at 7000 West Palmetto Park Road, Suite 505, Boca Raton, Florida 33433 (the ?Company?), and LUCAS VENTURES, LLC, an Arizona limited liability company (the ?Buyer?). WHEREA

Registration Rights Agreement, dated as of August 31, 2021, by and between the registrant and Lucas Ventures, LLC.

Exhibit 10.3 REGISTRATION RIGHTS AGREEMENT THIS REGISTRATION RIGHTS AGREEMENT (this ?Agreement?), dated as of August 31, 2021, is made by and between Simplicity Esports and Gaming Company, a Delaware corporation (the ?Company?), and Lucas Ventures, LLC (the ?Holder?). The Company and the Holder are hereinafter sometimes collectively referred to as the ?Parties? and each a ?Party? to this Agreement

List of Subsidiaries

EXHIBIT 21.1 List of Subsidiaries of Simplicity Esports and Gaming Company Entity Name Place of Organization Simplicity Esports, LLC * Florida PLAYlive Nation, Inc * Delaware PLAYlive Nation Holdings, LLC * Delaware Simplicity One Brasil Ltda ** Brazil Simplicity Happy Valley, LLC *** Oregon Simplicity Redmond, LLC *** Washington Simplicity El Paso, LLC**** Texas Simplicity Union Gap, LLC * Washin

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 Form 10-K [X] ANNUAL REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the fiscal year ended May 31, 2021 [ ] TRANSITION REPORT PURSUANT TO SECTIO

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 Form 10-K [X] ANNUAL REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the fiscal year ended May 31, 2021 [ ] TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission file number: 001-38188 SIMPLICITY ESPORTS AND GAMING

Securities Purchase Agreement, dated August 23, 2021, by and between the Company and Jefferson Street Capital LLC (35)

Exhibit 10.1 SECURITIES PURCHASE AGREEMENT This SECURITIES PURCHASE AGREEMENT (the ?Agreement?), dated as of August 23, 2021, by and between SIMPLICITY ESPORTS AND GAMING COMPANY, a Delaware corporation, with headquarters located at 7000 West Palmetto Park Road, Suite 505, Boca Raton, Florida 33433 (the ?Company?), and JEFFERSON STREET CAPITAL LLC, a New Jersey limited liability company, with its

Entry into a Material Definitive Agreement, Creation of a Direct Financial Obligation or an Obligation under an Off-Balance Sheet Arrangement of a Registrant, Financial Statements and Exhibits

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (date of earliest event reported): August 23, 2021 SIMPLICITY ESPORTS AND GAMING COMPANY (Exact name of registrant as specified in its charter) Delaware 001-38188 82-1231127 (State or other jurisdiction of incorporatio

Convertible Promissory Note, dated August 23, 2021, by the Company in favor of Jefferson Street Capital LLC (35)

Exhibit 10.2 NEITHER THE ISSUANCE AND SALE OF THE SECURITIES REPRESENTED BY THIS CERTIFICATE NOR THE SECURITIES INTO WHICH THESE SECURITIES ARE CONVERTIBLE HAVE BEEN REGISTERED UNDER THE SECURITIES ACT OF 1933, AS AMENDED, OR APPLICABLE STATE SECURITIES LAWS. THE SECURITIES MAY NOT BE OFFERED FOR SALE, SOLD, TRANSFERRED OR ASSIGNED (I) IN THE ABSENCE OF (A) AN EFFECTIVE REGISTRATION STATEMENT FOR

Common Stock Purchase Warrant, dated as of August 23, 2021, to Jefferson Street Capital, LLC (35)

Exhibit 10.4 NEITHER THIS SECURITY NOR THE SECURITIES FOR WHICH THIS SECURITY IS EXERCISABLE HAVE BEEN REGISTERED WITH THE SECURITIES AND EXCHANGE COMMISSION OR THE SECURITIES COMMISSION OF ANY STATE IN RELIANCE UPON AN EXEMPTION FROM REGISTRATION UNDER THE SECURITIES ACT OF 1933, AS AMENDED (THE ?SECURITIES ACT?), AND, ACCORDINGLY, MAY NOT BE OFFERED OR SOLD EXCEPT PURSUANT TO AN EFFECTIVE REGIST

Registration Rights Agreement, dated as of August 23, 2021, by and between the registrant and Jefferson Street Capital LLC.

Exhibit 10.3 REGISTRATION RIGHTS AGREEMENT THIS REGISTRATION RIGHTS AGREEMENT (this ?Agreement?), dated as of August 23, 2021, is made by and between Simplicity Esports and Gaming Company, a Delaware corporation (the ?Company?), and Jefferson Street Capital LLC, a New Jersey limited liability company (the ?Holder?). The Company and the Holder are hereinafter sometimes collectively referred to as t

Fourth Amendment to the Series A-2 Exchange Convertible Note entered into on August 19, 2021, by and between the registrant and Maxim Group LLC (34)

Exhibit 10.1 FOURTH AMENDMENT TO THE SERIES A-2 EXCHANGE CONVERTIBLE NOTE ISSUED ON DECEMBER 20, 2018 THIS FOURTH AMENDMENT to the Note (as defined below) (the ?Amendment?) is entered into on August 19, 2021 (the ?Effective Date?), by and between Simplicity Esports and Gaming Company, a Delaware corporation (the ?Company?), and Maxim Group LLC (the ?Holder? and collectively with the Company, the ?

Common Stock Purchase Warrant, dated as of August 4, 2021, to Maxim Group, LLC (34)

Exhibit 10.2 NEITHER THIS SECURITY NOR THE SECURITIES AS TO WHICH THIS SECURITY MAY BE EXERCISED HAVE BEEN REGISTERED WITH THE SECURITIES AND EXCHANGE COMMISSION OR THE SECURITIES COMMISSION OF ANY STATE IN RELIANCE UPON AN EXEMPTION FROM REGISTRATION UNDER THE SECURITIES ACT OF 1933, AS AMENDED (THE ?SECURITIES ACT?), AND, ACCORDINGLY, MAY NOT BE OFFERED OR SOLD EXCEPT PURSUANT TO AN EFFECTIVE RE

Entry into a Material Definitive Agreement, Financial Statements and Exhibits

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (date of earliest event reported): August 19, 2021 SIMPLICITY ESPORTS AND GAMING COMPANY (Exact name of registrant as specified in its charter) Delaware 001-38188 82-1231127 (State or other jurisdiction of incorporatio

List of Subsidiaries*

EXHIBIT 21.1 List of Subsidiaries of Simplicity Esports and Gaming Company Entity Name Place of Organization Simplicity Esports, LLC * Florida PLAYlive Nation, Inc * Delaware PLAYlive Nation Holdings, LLC * Delaware Simplicity One Brasil Ltda ** Brazil Simplicity Happy Valley, LLC *** Oregon Simplicity Redmond, LLC *** Washington Simplicity El Paso, LLC**** Texas Simplicity Union Gap, LLC * Washin

As filed with the Securities and Exchange Commission on July 15, 2021

As filed with the Securities and Exchange Commission on July 15, 2021 Registration No.

Simplicity Esports and Gaming Company Booked Record Setting Revenue from Gaming Centers this Month

Exhibit 99.1 Simplicity Esports and Gaming Company Booked Record Setting Revenue from Gaming Centers this Month The majority of Simplicity?s gaming centers are still operating at a reduced capacity. Boca Raton, Florida ? June 29, 2021 (GLOBE NEWSWIRE) ? Simplicity Esports and Gaming Company (OTCQB:WINR) (?Simplicity Esports?), announced that its esports gaming centers experienced record revenue in

Other Events, Financial Statements and Exhibits

8-K 1 form8-k.htm UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (date of earliest event reported): June 29, 2021 SIMPLICITY ESPORTS AND GAMING COMPANY (Exact name of registrant as specified in its charter) Delaware 001-38188 82-1231127 (State or other jurisdiction

Convertible Promissory Note, issued on June 16, 2021 and dated as of June 10, 2021, by the Company in favor of GS Capital Partners, LLC (33)

EX-10.4 5 ex10-4.htm Exhibit 10.4 NEITHER THE ISSUANCE AND SALE OF THE SECURITIES REPRESENTED BY THIS CERTIFICATE NOR THE SECURITIES INTO WHICH THESE SECURITIES ARE CONVERTIBLE HAVE BEEN REGISTERED UNDER THE SECURITIES ACT OF 1933, AS AMENDED, OR APPLICABLE STATE SECURITIES LAWS. THE SECURITIES MAY NOT BE OFFERED FOR SALE, SOLD, TRANSFERRED OR ASSIGNED (I) IN THE ABSENCE OF (A) AN EFFECTIVE REGIST

Securities Purchase Agreement, entered into on June 11, 2021 and dated as of June 10, 2021, by and between the Company and FirstFire Global Opportunities Fund, LLC (33)

Exhibit 10.1 SECURITIES PURCHASE AGREEMENT This SECURITIES PURCHASE AGREEMENT (the ?Agreement?), dated as of June 10 2021, by and between SIMPLICITY ESPORTS AND GAMING COMPANY, a Delaware corporation, with headquarters located at 7000 West Palmetto Park Road, Suite 505, Boca Raton, Florida 33433 (the ?Company?), and FIRSTFIRE GLOBAL OPPORTUNITIES FUND, LLC, a Delaware limited liability company, wi

Entry into a Material Definitive Agreement, Creation of a Direct Financial Obligation or an Obligation under an Off-Balance Sheet Arrangement of a Registrant, Financial Statements and Exhibits

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (date of earliest event reported): June 11, 2021 SIMPLICITY ESPORTS AND GAMING COMPANY (Exact name of registrant as specified in its charter) Delaware 001-38188 82-1231127 (State or other jurisdiction of incorporation)

Convertible Promissory Note, issued on June 11, 2021 and dated as of June 10, 2021, by the Company in favor of FirstFire Global Opportunities Fund LLC (33)

Exhibit 10.2 NEITHER THE ISSUANCE AND SALE OF THE SECURITIES REPRESENTED BY THIS CERTIFICATE NOR THE SECURITIES INTO WHICH THESE SECURITIES ARE CONVERTIBLE HAVE BEEN REGISTERED UNDER THE SECURITIES ACT OF 1933, AS AMENDED, OR APPLICABLE STATE SECURITIES LAWS. THE SECURITIES MAY NOT BE OFFERED FOR SALE, SOLD, TRANSFERRED OR ASSIGNED (I) IN THE ABSENCE OF (A) AN EFFECTIVE REGISTRATION STATEMENT FOR

Securities Purchase Agreement, entered into on June 16, 2021 and dated as of June 10, 2021, by and between the Company and GS Capital Partners, LLC (33)

Exhibit 10.3 SECURITIES PURCHASE AGREEMENT This SECURITIES PURCHASE AGREEMENT (the ?Agreement?), dated as of June 10, 2021, by and between SIMPLICITY ESPORTS AND GAMING COMPANY, a Delaware corporation, with headquarters located at 7000 West Palmetto Park Road, Suite 505, Boca Raton, Florida 33433 (the ?Company?), and GS CAPITAL PARTNERS, LLC, a Delaware limited liability company, with its address

As filed with the Securities and Exchange Commission on June 4, 2021

As filed with the Securities and Exchange Commission on June 4, 2021 Registration No.

Simplicity Esports and Gaming Company

Exhibit 99.1 Simplicity Esports and Gaming Company Updates Expansion of its Esports Gaming Center Footprint Simplicity Esports already has the largest footprint of esports gaming center in the U.S. Boca Raton, Florida ? May 24, 2021 (GLOBE NEWSWIRE) ? Simplicity Esports and Gaming Company (OTCQB:WINR) (?Simplicity Esports?), announced today that it intends to continue the expansion of its corporat

Other Events, Financial Statements and Exhibits

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (date of earliest event reported): May 24, 2021 SIMPLICITY ESPORTS AND GAMING COMPANY (Exact name of registrant as specified in its charter) Delaware 001-38188 82-1231127 (State or other jurisdiction of incorporation)

Investor presentation of the registrant dated May 2021.

Exhibit 99.1

Regulation FD Disclosure, Departure of Directors or Certain Officers; Election of Directors; Appointment of Certain Officers; Compensatory Arrangements of Certain Officers, Other Events, Financial Statements and Exhibits

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (date of earliest event reported): May 7, 2021 SIMPLICITY ESPORTS AND GAMING COMPANY (Exact name of registrant as specified in its charter) Delaware 001-38188 82-1231127 (State or other jurisdiction of incorporation) (

Employment Agreement by and between the Company and Nancy Hennessey, entered into on May 11, 2021 and effective as of May 17, 2021 (32) †

Exhibit 10.1 EMPLOYMENT AGREEMENT This Employment Agreement (the ?Agreement?) is made and entered into as of May 17, 2021 (the ?Effective Date?), by and between Nancy Hennessey, an individual, (the ?Executive?) and Simplicity Esports and Gaming Company, a Delaware corporation (the ?Company?). The Company and the Executive may be referred to herein individually as a ?Party? and collectively as the

125,000 Shares of Common Stock

Filed Pursuant to Rule 424(b)(3) Registration No. 333-255584 125,000 Shares of Common Stock This prospectus (this ?Prospectus?) relates to the offer and sale from time to time of up to 125,000 (1,000,000 pre-reverse split) shares of common stock, par value $0.0001, of Simplicity Esports and Gaming Company, a Delaware corporation, by Tiger Trout Capital Puerto Rico, LLC, a Puerto Rico limited liabi

Other Events, Financial Statements and Exhibits

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (date of earliest event reported): May 10, 2021 SIMPLICITY ESPORTS AND GAMING COMPANY (Exact name of registrant as specified in its charter) Delaware 001-38188 82-1231127 (State or other jurisdiction (Commission (I.R.S

Simplicity Esports and Gaming Company

EX-99.1 2 ex99-1.htm Exhibit 99.1 Simplicity Esports and Gaming Company Booked Record Setting Revenue from Gaming Centers The corporate owned gaming center revenues combined with royalties and fees from franchisee owned locations set a record in March and again in April. Boca Raton, Florida — May 10, 2021 (GLOBE NEWSWIRE) — Simplicity Esports and Gaming Company (OTCQB:WINR) (“Simplicity Esports”),

SIMPLICITY ESPORTS AND GAMING COMPANY 7000 W. Palmetto Park Rd., Suite 505 Boca Raton, FL 33433 May 6, 2021

SIMPLICITY ESPORTS AND GAMING COMPANY 7000 W. Palmetto Park Rd., Suite 505 Boca Raton, FL 33433 May 6, 2021 CORRESPONDENCE FILING VIA EDGAR Mr. Donald Field Office of Trade & Services U.S. Securities and Exchange Commission 100 F Street, N.E. Washington, D.C. 20549 Re: Simplicity Esports and Gaming Company Registration Statement Filed on Resale Form S-1 (File No. 333-255584) Dear Mr. Field: On beh

List of Subsidiaries*

EX-21.1 3 ex21-1.htm Exhibit 21.1 List of Subsidiaries of Simplicity Esports and Gaming Company Entity Name Place of Organization Simplicity Esports, LLC * Florida PLAYlive Nation, Inc * Delaware PLAYlive Nation Holdings, LLC * Delaware Simplicity One Brasil Ltda ** Brazil Simplicity Happy Valley, LLC *** Oregon Simplicity Redmond, LLC *** Washington Simplicity El Paso, LLC**** Texas Simplicity Un

Registration Statement -

As filed with the Securities and Exchange Commission on April 28, 2021 Registration No.

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As filed with the Securities and Exchange Commission on April 16, 2021 Registration No.

List of Subsidiaries*

EX-21.1 3 ex21-1.htm EXHIBIT 21.1 List of Subsidiaries of Simplicity Esports and Gaming Company Entity Name Place of Organization Simplicity Esports, LLC * Florida PLAYlive Nation, Inc * Delaware PLAYlive Nation Holdings, LLC * Delaware Simplicity One Brasil Ltda ** Brazil Simplicity Happy Valley, LLC *** Oregon Simplicity Redmond, LLC *** Washington Simplicity El Paso, LLC**** Texas Simplicity Un

Third Amendment to the Series A-2 Exchange Convertible Note entered into on April 14, 2021, by and between the registrant and Maxim Group LLC (31)

Exhibit 10.11 THIRD AMENDMENT TO THE SERIES A-2 EXCHANGE CONVERTIBLE NOTE ISSUED ON DECEMBER 20, 2018 THIS THIRD AMENDMENT to the Note (as defined below) (the ?Amendment?) is entered into on April 14, 2021 (the ?Effective Date?), by and between Simplicity Esports and Gaming Company, a Delaware corporation (the ?Company?), and Maxim Group LLC (the ?Holder? and collectively with the Company, the ?Pa

Quarterly Report -

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q [X] QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended February 28, 2021 or [ ] TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission File Number: 001-38188 SIMPLICITY ES

Stock Purchase Agreement, dated as of March 31, 2021, by and between the Company and Tiger Trout Capital Puerto Rico, LLC (31)

Exhibit 10.1 Stock Purchase Agreement By and Among Simplicity Esports and Gaming Company And Tiger Trout Capital Puerto Rico, LLC Dated as of March [31], 2021 TABLE OF CONTENTS Article I. DEFINITIONS 1 Section 1.01 Definitions. 1 Section 1.02 Interpretive Provisions. 3 Article II. PURCHASE AND SALE 3 Section 2.01 Purchase and Sale. 3 Section 2.02 Closings. 4 Section 2.03 Deliverables and Actions o

Entry into a Material Definitive Agreement, Financial Statements and Exhibits

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (date of earliest event reported): March 31, 2021 SIMPLICITY ESPORTS AND GAMING COMPANY (Exact name of registrant as specified in its charter) Delaware 001-38188 82-1231127 (State or other jurisdiction of incorporation

Regulation FD Disclosure, Departure of Directors or Certain Officers; Election of Directors; Appointment of Certain Officers; Compensatory Arrangements of Certain Officers, Other Events, Financial Statements and Exhibits

8-K 1 form8-k.htm UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (date of earliest event reported): March 18, 2021 SIMPLICITY ESPORTS AND GAMING COMPANY (Exact name of registrant as specified in its charter) Delaware 001-38188 82-1231127 (State or other jurisdictio

Simplicity Esports and Gaming Company Strengthens C-Suite by Hiring Former Executive Director of Accounting and Finance for MGM Growth Properties as new CFO

EX-99.1 4 ex99-1.htm Exhibit 99.1 Simplicity Esports and Gaming Company Strengthens C-Suite by Hiring Former Executive Director of Accounting and Finance for MGM Growth Properties as new CFO Boca Raton, Florida — March 29, 2021 (GLOBE NEWSWIRE) —Simplicity Esports and Gaming Company (OTCQB:WINR) (“Simplicity Esports”) announced that, in an effort to strengthen and reinforce its internal controls a

Employment Agreement, entered into on March 23, 2021 and effective March 29, 2021, by and between the Company and Knicks Lau (29) †

Exhibit 10.2 EMPLOYMENT AGREEMENT This Employment Agreement (the ?Agreement?) is made and entered into as of March 29, 2021 (the ?Effective Date?), by and between Knicks Lau, an individual, (the ?Executive?) and Simplicity Esports and Gaming Company, a Delaware corporation (the ?Company?). The Company and the Executive may be referred to herein individually as a ?Party? and collectively as the ?Pa

Employment Agreement, entered into on March 25, 2021 and effective March 29, 2021, by and between the Company and Roman Franklin (29) †

EX-10.1 2 ex10-1.htm Exhibit 10.1 EMPLOYMENT AGREEMENT This Employment Agreement (the “Agreement”) is made and entered into as of March 29, 2021 (the “Effective Date”), by and between Roman Franklin, an individual, (the “Executive”) and Simplicity Esports and Gaming Company, a Delaware corporation (the “Company”). The Company and the Executive may be referred to herein individually as a “Party” an

Exchange Agreement by and between the registrant, Anthony L.G., PLLC and Laura Anthony, dated as of November 25, 2020.

EX-99.2 5 ex99-2.htm Exhibit 99.2 EXCHANGE AGREEMENT This EXCHANGE AGREEMENT (this “Agreement”) is made and entered into effective as of November 25, 2020 (the “Effective Date”), by and between SIMPLICITY ESPORTS AND GAMING COMPANY, a Delaware corporation (the “Company”), Anthony L.G., PLLC, a Florida professional limited liability company (the “Firm”) and Laura Anthony, the sole equity holder of

Exchange Agreement by and between the registrant and Laura Anthony, dated as of March 2, 2021.

Exhibit 99.3 EXCHANGE AGREEMENT This EXCHANGE AGREEMENT (this ?Agreement?) is made and entered into effective as of March 2, 2021 (the ?Effective Date?), by and between SIMPLICITY ESPORTS AND GAMING COMPANY, a Delaware corporation (the ?Company?) and Laura Anthony, the sole equity holder of Anthony L.G., PLLC. W I T N E S S E T H : WHEREAS, as of March 2, 2021, Laura Anthony is owed $97,155.00 by

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AS FILED WITH THE SECURITIES AND EXCHANGE COMMISSION ON MARCH 18, 2021 Registration Statement No.

Exchange Agreement by and between the registrant, Anthony L.G., PLLC and Laura Anthony, dated as of June 3, 2020.

EX-99.1 4 ex99-1.htm Exhibit 99.1 EXCHANGE AGREEMENT This EXCHANGE AGREEMENT (this “Agreement”) is made and entered into effective as of June 3, 2020 (the “Effective Date”), by and between SIMPLICITY ESPORTS AND GAMING COMPANY, a Delaware corporation (the “Company”) and Anthony L.G., PLLC, a Florida professional limited liability company (the “Firm”) and Laura Anthony, the sole equity holder of An

Promissory Note dated March 10, 2021, issued by the Company to FirstFire Global Opportunities Fund, LLC (28)

Exhibit 10.1 NEITHER THE ISSUANCE AND SALE OF THE SECURITIES REPRESENTED BY THIS CERTIFICATE NOR THE SECURITIES INTO WHICH THESE SECURITIES ARE CONVERTIBLE HAVE BEEN REGISTERED UNDER THE SECURITIES ACT OF 1933, AS AMENDED, OR APPLICABLE STATE SECURITIES LAWS. THE SECURITIES MAY NOT BE OFFERED FOR SALE, SOLD, TRANSFERRED OR ASSIGNED (I) IN THE ABSENCE OF (A) AN EFFECTIVE REGISTRATION STATEMENT FOR

Entry into a Material Definitive Agreement, Creation of a Direct Financial Obligation or an Obligation under an Off-Balance Sheet Arrangement of a Registrant, Financial Statements and Exhibits

8-K 1 form8-k.htm UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (date of earliest event reported): March 10, 2021 SIMPLICITY ESPORTS AND GAMING COMPANY (Exact name of registrant as specified in its charter) Delaware 001-38188 82-1231127 (State or other jurisdictio

Securities Purchase Agreement dated March 10, 2021, by and between the Company and FirstFire Global Opportunities Fund, LLC (28)

Exhibit 10.2 SECURITIES PURCHASE AGREEMENT This SECURITIES PURCHASE AGREEMENT (the ?Agreement?), dated as of March 10, 2021, by and between SIMPLICITY ESPORTS AND GAMING COMPANY, a Delaware corporation, with headquarters located at 7000 W. Palmetto Park Rd., Suite 505, Boca Raton, FL 33433 (the ?Company?), and FIRSTFIRE GLOBAL OPPORTUNITIES FUND, LLC, a Delaware limited liability company, with its

Entry into a Material Definitive Agreement, Creation of a Direct Financial Obligation or an Obligation under an Off-Balance Sheet Arrangement of a Registrant, Financial Statements and Exhibits

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (date of earliest event reported): February 19, 2021 SIMPLICITY ESPORTS AND GAMING COMPANY (Exact name of registrant as specified in its charter) Delaware 001-38188 82-1231127 (State or other jurisdiction of incorporat

Securities Purchase Agreement dated February 19, 2021, by and between the Company and the Holder (27)

Exhibit 10.2 SECURITIES PURCHASE AGREEMENT This SECURITIES PURCHASE AGREEMENT (the ?Agreement?), dated as of February 19, 2021, by and between SIMPLICITY ESPORTS AND GAMING COMPANY, a Delaware corporation, with headquarters located at 7000 W. Palmetto Park Rd., Suite 505, Boca Raton, FL 33433 (the ?Company?), and , a Delaware limited partnership, with its address at (the ?Buyer?). WHEREAS: A. The

Promissory Note dated February 19, 2021, issued by the Company to the Holder (27)

Exhibit 10.1 NEITHER THE ISSUANCE AND SALE OF THE SECURITIES REPRESENTED BY THIS CERTIFICATE NOR THE SECURITIES INTO WHICH THESE SECURITIES ARE CONVERTIBLE HAVE BEEN REGISTERED UNDER THE SECURITIES ACT OF 1933, AS AMENDED, OR APPLICABLE STATE SECURITIES LAWS. THE SECURITIES MAY NOT BE OFFERED FOR SALE, SOLD, TRANSFERRED OR ASSIGNED (I) IN THE ABSENCE OF (A) AN EFFECTIVE REGISTRATION STATEMENT FOR

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13G Under the Securities Exchange Act of 1934 SIMPLICITY ESPORTS AND GAMING COMPANY (Name of Issuer) Common Stock - $0.0001 par value (Title of Class of Securities) 8288

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13G Under the Securities Exchange Act of 1934 SIMPLICITY ESPORTS AND GAMING COMPANY (Name of Issuer) Common Stock - $0.0001 par value (Title of Class of Securities) 82887P209 (CUSIP Number) December 31, 2020 (Date of Event which Requires Filing of this Statement) Check the appropriate box to designate the rule pursuan

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13G/A Under the Securities Exchange Act of 1934 (Amendment No. 4)*

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13G/A Under the Securities Exchange Act of 1934 (Amendment No. 4)* Simplicity Esports and Gaming Company (Name of Issuer) Common Stock (Title of Class of Securities) 82887P100 (CUSIP Number) December 31, 2020 (Date of Event which Requires Filing of this Statement) Check the appropriate box to designate the rule pursua

Simplicity Esports and Gaming Company

SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13G/A Under the Securities Exchange Act of 1934 (Amendment No. 2)* Simplicity Esports and Gaming Company (Name of Issuer) Common Stock, par value $0.0001 per share (Title of Class of Securities) 82887P209 (CUSIP Number) December 31, 2020 (Date of Event Which Requires Filing of this Statement) Check the appropriate box to designate

List of Subsidiaries*

EXHIBIT 21.1 List of Subsidiaries of Simplicity Esports and Gaming Company Entity Name Place of Organization Simplicity Esports, LLC * Florida PLAYlive Nation, Inc * Delaware PLAYlive Nation Holdings, LLC * Delaware Simplicity One Brasil Ltda ** Brazil Simplicity Happy Valley, LLC *** Oregon Simplicity Redmond, LLC *** Washington Simplicity El Paso, LLC**** Texas Simplicity Union Gap, LLC * Washin

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As filed with the Securities and Exchange Commission on January 19, 2021 Registration No.

Quarterly Report -

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q [X] QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended November 30, 2020 or [ ] TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission File Number: 001-38188 SIMPLICITY ES

Entry into a Material Definitive Agreement, Creation of a Direct Financial Obligation or an Obligation under an Off-Balance Sheet Arrangement of a Registrant, Financial Statements and Exhibits -

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (date of earliest event reported): November 25, 2020 SIMPLICITY ESPORTS AND GAMING COMPANY (Exact name of registrant as specified in its charter) Delaware 001-38188 82-1231127 (State or other jurisdiction of incorporat

Self-Amortization Promissory Note dated November 23, 2020, issued by the Company to an accredited investor (26)

Exhibit 10.1 NEITHER THE ISSUANCE AND SALE OF THE SECURITIES REPRESENTED BY THIS CERTIFICATE NOR THE SECURITIES INTO WHICH THESE SECURITIES ARE CONVERTIBLE HAVE BEEN REGISTERED UNDER THE SECURITIES ACT OF 1933, AS AMENDED, OR APPLICABLE STATE SECURITIES LAWS. THE SECURITIES MAY NOT BE OFFERED FOR SALE, SOLD, TRANSFERRED OR ASSIGNED (I) IN THE ABSENCE OF (A) AN EFFECTIVE REGISTRATION STATEMENT FOR

Common Stock Purchase Warrant dated November 23, 2020, issued by the Company to an accredited investor (26)

EX-10.3 4 ex10-3.htm Exhibit 10.3 NEITHER THIS SECURITY NOR THE SECURITIES AS TO WHICH THIS SECURITY MAY BE EXERCISED HAVE BEEN REGISTERED WITH THE SECURITIES AND EXCHANGE COMMISSION OR THE SECURITIES COMMISSION OF ANY STATE IN RELIANCE UPON AN EXEMPTION FROM REGISTRATION UNDER THE SECURITIES ACT OF 1933, AS AMENDED (THE “SECURITIES ACT”), AND, ACCORDINGLY, MAY NOT BE OFFERED OR SOLD EXCEPT PURSUA

Securities Purchase Agreement dated November 23, 2020, by and between the Company and an accredited investor (26)

Exhibit 10.2 SECURITIES PURCHASE AGREEMENT This SECURITIES PURCHASE AGREEMENT (the “Agreement”), dated as of November 23, 2020, by and between SIMPLICITY ESPORTS AND GAMING COMPANY, a Delaware corporation, with headquarters located at 7000 W. Palmetto Park Rd., Suite 505, Boca Raton, FL 33433 (the “Company”), and , a Delaware limited partnership, with its address at 48 Parker Road, Wellesley, MA 0

Certificate of Amendment to the Company’s Third Amended and Restated Certificate of Incorporation, filed with the Delaware Secretary of State on November 17, 2020 (25)

Exhibit 3.1 STATE OF DELAWARE CERTIFICATE OF AMENDMENT TO THIRD AMENDED AND RESTATED CERTIFICATE OF INCORPORATION, AS AMENDED, OF SIMPLICITY ESPORTS AND GAMING COMPANY Under Section 242 of the Delaware General Corporation Law Simplicity Esports and Gaming Company, a corporation organized and existing under and by virtue of the General Corporation Law of the State of Delaware (the “Corporation”), d

Amendments to Articles of Incorporation or Bylaws; Change in Fiscal Year, Financial Statements and Exhibits -

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (date of earliest event reported): November 17, 2020 SIMPLICITY ESPORTS AND GAMING COMPANY (Exact name of registrant as specified in its charter) Delaware 001-38188 82-1231127 (State or other jurisdiction of incorporat

Certificate of Amendment to the Company’s Third Amended and Restated Certificate of Incorporation, filed with the Delaware Secretary of State on November 2, 2020 (24)

Exhibit 3.1 STATE OF DELAWARE CERTIFICATE OF AMENDMENT TO THIRD AMENDED AND RESTATED CERTIFICATE OF INCORPORATION, AS AMENDED, OF SIMPLICITY ESPORTS AND GAMING COMPANY Under Section 242 of the Delaware General Corporation Law Simplicity Esports and Gaming Company, a corporation organized and existing under and by virtue of the General Corporation Law of the State of Delaware (the “Corporation”), d

Amendments to Articles of Incorporation or Bylaws; Change in Fiscal Year, Financial Statements and Exhibits -

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (date of earliest event reported): November 2, 2020 SIMPLICITY ESPORTS AND GAMING COMPANY (Exact name of registrant as specified in its charter) Delaware 001-38188 82-1231127 (State or other jurisdiction of incorporati

List of Subsidiaries*

EXHIBIT 21.1 List of Subsidiaries of Simplicity Esports and Gaming Company Entity Name Place of Organization Simplicity Esports, LLC * Florida PLAYlive Nation, Inc * Delaware Simplicity One Brasil Ltda ** Brazil Simplicity Happy Valley, LLC *** Oregon Simplicity Redmond, LLC *** Washington * 100% owned subsidiary of Simplicity Esports and Gaming Company **76% owned subsidiary of Simplicity Esports

Form of Representative’s Warrant (39)

EXHIBIT 4.6 Form of Representative’s Warrant Agreement THE REGISTERED HOLDER OF THIS PURCHASE WARRANT BY ITS ACCEPTANCE HEREOF, AGREES THAT IT WILL NOT SELL, TRANSFER, ASSIGN, PLEDGE OR HYPOTHECATE, OR BE THE SUBJECT OF ANY HEDGING, SHORT SALE, DERIVATIVE, PUT, OR CALL TRANSACTION THAT WOULD RESULT IN THE EFFECTIVE ECONOMIC DISPOSITION OF THIS PURCHASE WARRANT OR THE UNDERLYING SECURITIES FOR A PE

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As filed with the Securities and Exchange Commission on October 23, 2020 Registration No.

Form of Warrant Agent Agreement by and between the Company and Continental Stock Transfer & Trust Company (39)

EXHIBIT 4.5 WARRANT AGENT AGREEMENT WARRANT AGENT AGREEMENT (this “Warrant Agreement”) dated as of , 2020 (the “Issuance Date”) between Simplicity Esports and Gaming Company, a company incorporated under the laws of the State of Delaware (the “Company”), and Continental Stock Transfer & Trust Company, a New York corporation (the “Warrant Agent”). WHEREAS, pursuant to the terms of that certain Unde

Form of Underwriting Agreement*

EXHIBIT 1.1 UNITS EACH UNIT CONSISTING OF ONE SHARE of Common Stock and ONE Warrant TO PURCHASE ONE SHARE OF COMMON STOCK SIMPLICITY ESPORTS AND GAMING COMPANY UNDERWRITING AGREEMENT , 2020 Maxim Group LLC Investment Banking 405 Lexington Avenue, 2nd Fl. New York, New York 10174 As Representative of the Several Underwriters, if any, named in Schedule I hereto Ladies and Gentlemen: The undersigned,

Quarterly Report -

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q [X] QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended August 31, 2020 or [ ] TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission File Number: 001-38188 SIMPLICITY ESPO

Certificate of Amendment to Third Amended and Restated Certificate of Incorporation, as amended, filed with Delaware Secretary of State on September 18, 2020.

Exhibit 3.2 STATE OF DELAWARE CERTIFICATE OF AMENDMENT TO THIRD AMENDED AND RESTATED CERTIFICATE OF INCORPORATION, AS AMENDED, OF SIMPLICITY ESPORTS AND GAMING COMPANY Under Section 242 of the Delaware General Corporation Law Simplicity Esports and Gaming Company, a corporation organized and existing under and by virtue of the General Corporation Law of the State of Delaware (the “Corporation”), d

SIMPLICITY ESPORTS AND GAMING COMPANY 6,449,000 Shares of Common Stock Underlying Warrants 6,203,969 Shares of Common Stock for Resale by Selling Securityholders 261,500 Warrants to Purchase Common Stock for Resale by Selling Securityholders

PROSPECTUS Filed Pursuant to Rule 424(b)(3) Registration No. 333-228906 SIMPLICITY ESPORTS AND GAMING COMPANY 6,449,000 Shares of Common Stock Underlying Warrants 6,203,969 Shares of Common Stock for Resale by Selling Securityholders 261,500 Warrants to Purchase Common Stock for Resale by Selling Securityholders This prospectus relates to the issuance by us of up to 6,449,000 shares of our common

Certificate of Amendment to the Company’s Third Amended and Restated Certificate of Incorporation, filed with the Delaware Secretary of State on October 12, 2020 (23)

Exhibit 3.1 STATE OF DELAWARE CERTIFICATE OF AMENDMENT TO THIRD AMENDED AND RESTATED CERTIFICATE OF INCORPORATION, AS AMENDED, OF SIMPLICITY ESPORTS AND GAMING COMPANY Under Section 242 of the Delaware General Corporation Law Simplicity Esports and Gaming Company, a corporation organized and existing under and by virtue of the General Corporation Law of the State of Delaware (the “Corporation”), d

Amendments to Articles of Incorporation or Bylaws; Change in Fiscal Year, Financial Statements and Exhibits -

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (date of earliest event reported): October 12, 2020 SIMPLICITY ESPORTS AND GAMING COMPANY (Exact name of registrant as specified in its charter) Delaware 001-38188 82-1231127 (State or other jurisdiction of incorporati

Amendments to Articles of Incorporation or Bylaws; Change in Fiscal Year, Financial Statements and Exhibits -

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (date of earliest event reported): September 29, 2020 SIMPLICITY ESPORTS AND GAMING COMPANY (Exact name of registrant as specified in its charter) Delaware 001-38188 82-1231127 (State or other jurisdiction of incorpora

Certificate of Amendment to the Company’s Third Amended and Restated Certificate of Incorporation, filed with the Delaware Secretary of State on September 18, 2020 (21)

Exhibit 3.4 STATE OF DELAWARE CERTIFICATE OF AMENDMENT TO THIRD AMENDED AND RESTATED CERTIFICATE OF INCORPORATION, AS AMENDED, OF SIMPLICITY ESPORTS AND GAMING COMPANY Under Section 242 of the Delaware General Corporation Law Simplicity Esports and Gaming Company, a corporation organized and existing under and by virtue of the General Corporation Law of the State of Delaware (the “Corporation”), d

Certificate of Amendment to the Company’s Third Amended and Restated Certificate of Incorporation, filed with the Delaware Secretary of State on September 29, 2020 (22)

Exhibit 3.1 STATE OF DELAWARE AMENDED AND RESTATED CERTIFICATE OF AMENDMENT TO THIRD AMENDED AND RESTATED CERTIFICATE OF INCORPORATION, AS AMENDED, OF SIMPLICITY ESPORTS AND GAMING COMPANY Under Section 242 of the Delaware General Corporation Law Simplicity Esports and Gaming Company, a corporation organized and existing under and by virtue of the General Corporation Law of the State of Delaware (