Sec Form 4 Filing - Kaplan Jed Philip @ SIMPLICITY ESPORTS & GAMING Co - 2018-12-31

FORM 4 Check this box if no longer subject to Section 16. Form 4 or Form 5 obligations may continue. See Instruction 1(b).

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 STATEMENT OF CHANGES IN BENEFICIAL OWNERSHIP Filed pursuant to Section 16(a) of the Securities Exchange Act of 1934, Section 17(a) of the Public Utility Holding Company Act of 1935 or Section 30(h) of the Investment Company Act of 1940

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1. Name and Address of Reporting Person Kaplan Jed Philip 2. Issuer Name and Ticker or Trading Symbol SIMPLICITY ESPORTS & GAMING Co [ WINR] 5. Relationship of Reporting Person(s) to Issuer (Check all applicable) X __ Director _____ 10% Owner X __ Officer (give title below) _____ Other (specify below) CEO and Interim CFO (Last) (First) (Middle) C/O SIMPLICITY ESPORTS & GAMING COMPANY, 7000 W. PALMETTO PARK RD., SUITE 505 3. Date of Earliest Transaction (MM/DD/YY) 12/31/2018 (Street) BOCA RATON, FL33433 4. If Amendment, Date Original Filed (MM/DD/YY) 6. Individual or Joint/Group Filing (Check Applicable Line) __ X __ Form filed by One Reporting Person _____ Form filed by More than One Reporting Person (City) (State) (Zip)

Table I - Non-Derivative Securities Acquired, Disposed of, or Beneficially Owned 1.Title of Security (Instr. 3) 2. Transaction Date (MM/DD/YY) 2A. Deemed Execution Date, if any (MM/DD/YY) 3. Transaction Code (Instr. 8) 4. Securities Acquired (A) or Disposed of (D) (Instr. 3, 4 and 5) 5. Amount of Securities Beneficially Owned Following Reported Transaction(s) (Instr. 3 and 4) 6. Ownership Form: Direct (D) or Indirect (I) (Instr. 4) 7. Nature of Indirect Beneficial Ownership (Instr. 4) Code V Amount (A) or (D) Price Common Stock ( 1 ) 12/31/2018 A( 2 ) 5,121 A $ 0 5,121 D Common Stock 12/31/2018 A( 2 ) 6,025 A $ 0 11,146 D Common Stock 01/08/2019 A( 2 ) 9,424 A $ 0 20,570 D Common Stock 01/08/2019 A( 2 ) 11,088 A $ 0 31,658 D Common Stock 01/08/2019 A( 2 ) 8,750 A $ 0 40,408 D ( 3 ) Common Stock 03/27/2019 A( 2 ) 26,927 A $ 0 67,335 D Common Stock 03/27/2019 A( 2 ) 31,679 A $ 0 99,014 D Common Stock 03/27/2019 A( 2 ) 25,000 A $ 0 124,014 D ( 3 ) Common Stock 03/27/2019 A( 2 ) 2,500 A $ 0 126,514 D ( 3 ) Common Stock 05/31/2019 P( 4 ) 6,250 A $ 16 132,764 D Common Stock 09/17/2019 A( 2 ) 8,750 A $ 0 141,514 D ( 3 ) Common Stock 07/29/2020 A( 2 ) 8,750 A $ 0 150,264 D Common Stock 07/30/2020 A( 2 ) 31,250 A $ 0 181,514 D Common Stock 08/21/2020 A( 2 ) 3,750 A $ 0 185,264 D Common Stock 08/31/2020 A( 2 ) 1,875 A $ 0 187,139 D Common Stock 09/30/2020 A( 2 ) 1,875 A $ 0 189,014 D Common Stock 10/30/2020 A( 2 ) 1,875 A $ 0 190,889 D Common Stock 11/18/2020 G( 5 ) 25,000 D $ 0 165,889 D ( 3 ) Common Stock 11/30/2020 A( 2 ) 1,875 A $ 0 167,764 D Common Stock 12/23/2020 G( 5 ) 5,000 D $ 0 162,764 D ( 3 ) Common Stock 12/31/2020 A( 2 ) 1,875 A $ 0 164,639 D Common Stock 01/04/2021 A( 2 ) 50,000 A $ 0 214,639 D Common Stock 11/18/2020 A( 2 ) 25,000 A $ 0 25,000 I See footnote ( 6 ) Common Stock 11/24/2020 A( 2 ) 10,000 A $ 0 35,000 I See footnote ( 6 ) Common Stock 12/23/2020 A( 2 ) 5,000 A $ 0 40,000 I See footnote ( 6 ) Common Stock 12/29/2020 A( 2 ) 3,000 A $ 0 43,000 I See footnote ( 6 ) Common Stock 12/31/2018 A 302 A $ 0 302 I By Spouse Common Stock 01/08/2019 A 555 A $ 0 857 I By Spouse Common Stock 03/27/2019 A 1,584 A $ 0 2,441 I By Spouse

Table II - Derivative Securities Acquired, Disposed of, or Beneficially Owned ( e.g. , puts, calls, warrants, options, convertible securities) 1. Title of Derivative Security (Instr. 3) 2. Conversion or Exercise Price of Derivative Security 3. Transaction Date (MM/DD/YY) 3A. Deemed Execution Date, if any (MM/DD/YY) 4. Transaction Code (Instr. 8) 5. Number of Derivative Securities Acquired (A) or Disposed of (D) (Instr. 3, 4, and 5) 6. Date Exercisable and Expiration Date (MM/DD/YY) 7. Title and Amount of Underlying Securities (Instr. 3 and 4) 8. Price of Derivative Security (Instr. 5) 9. Number of Derivative Securities Beneficially Owned Following Reported Transaction(s) (Instr. 4) 10. Ownership Form of Derivative Security: Direct (D) or Indirect (I) (Instr. 4) 11. Nature of Indirect Beneficial Ownership (Instr. 4) Code V (A) (D) Date Exercisable Expiration Date Title Amount or Number of Shares Warrant $ 0.5 05/31/2019 P( 4 ) 6,250 05/31/2019 05/31/2024 Common Stock 6,250 $ 16 6,250 D

Reporting Owners Reporting Owner Name / Address Relationships Director 10% Owner Officer Other Kaplan Jed Philip C/O SIMPLICITY ESPORTS & GAMING COMPANY 7000 W. PALMETTO PARK RD., SUITE 505 BOCA RATON, FL33433 X CEO and Interim CFO Signatures /s/ Jed Kaplan 02/01/2021 Signature of Reporting Person Date

Explanation of Responses:

( 1 )The share information in this Form 4 has been adjusted to give effect to the 1-for-8 reverse stock split of the issuer's common stock, which was effective on November 20, 2020. ( 2 )Represents a grant by the issuer to the reporting person. The grant was approved by the issuer's Board of Directors. ( 3 )Held jointly with spouse. ( 4 )Pursuant to a private placement, the reporting person purchased 6,250 "units" of the issuer's securities at a purchase price of $16.00 per unit. Each unit consisted of (i) one share of the issuer's common stock, and (ii) a warrant to purchase one share of the issuer's common stock, exercisable at a price of $0.50 per share, exercisable at any time within five years of issuance. ( 5 )Bona fide gift to Kaplan Charitable Foundation, of which the reporting person serves as trustee. ( 6 )Held by Kaplan Charitable Foundation, of which the reporting person serves as trustee.

Reminder: Report on a separate line for each class of securities beneficially owned directly or indirectly.

* If the form is filed by more than one reporting person, see Instruction 4(b)(v).

** Intentional misstatements or omissions of facts constitute Federal Criminal Violations. See 18 U.S.C. 1001 and 15 U.S.C. 78ff(a).

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