Sec Form 4 Filing - MATHIS SCOTT L @ Gaucho Group Holdings, Inc. - 2021-07-06

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 MATHIS SCOTT L 2. Issuer Name and Ticker or Trading Symbol Gaucho Group Holdings, Inc. [ VINO] 5. Relationship of Reporting Person(s) to Issuer (Check all applicable) X __ Director _____ 10% Owner X __ Officer (give title below) _____ Other (specify below) President, CEO, Chair. & Dir. (Last) (First) (Middle) 1445 16TH STREET, SUITE 403 3. Date of Earliest Transaction (MM/DD/YY) 07/06/2021 (Street) MIAMI BEACH,, FL33139 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 07/06/2021 A 522 A $ 0 17,992 I See Footnote ( 1 ) Common Stock 23,771 D Common Stock 251,829 I See Footnote ( 2 )

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 Stock Option $ 5.78 ( 3 ) 07/08/2024 Common Stock 147,326 147,326 D Stock Option $ 5.78 ( 4 ) 01/31/2024 Common Stock 30,000 30,000 D Stock Option $ 8.09 ( 5 ) 09/20/2023 Common Stock 48,334 48,334 D Stock Option $ 11.55 ( 6 ) 02/14/2023 Common Stock 66,667 66,667 D Stock Option $ 16.5 ( 7 ) 12/17/2022 Common Stock 20,000 20,000 D

Reporting Owners Reporting Owner Name / Address Relationships Director 10% Owner Officer Other MATHIS SCOTT L 1445 16TH STREET, SUITE 403 MIAMI BEACH,, FL33139 X President, CEO, Chair. & Dir. Signatures /s/ Scott L. Mathis 11/01/2021 Signature of Reporting Person Date

Explanation of Responses:

( 1 )Shares held by Mr. Mathis' 401(k) account. ( 2 )Shares held by The WOW Group, LLC, of which Mr. Mathis is a managing member and of which Mr. Mathis is a controlling member. ( 3 )Stock options granted pursuant to 2018 Equity Incentive Plan; options to acquire 36,832 shares vest on 7/8/20; thereafter options to acquire 9,208 shares vest every three months in equal installments. ( 4 )Stock options granted pursuant to 2018 Equity Incentive Plan; options to acquire 7,500 shares vest on 1/31/20; thereafter options to acquire 1,875 shares vest every three months in equal installments. ( 5 )Stock options granted pursuant to 2018 Equity Incentive Plan; options to acquire 12,084 shares vest on 9/20/19; thereafter options to acquire 3,021 shares vest every three months in equal installments with the last installment of 3,020 vesting on 9/20/22. ( 6 )Stock options granted pursuant to 2016 Equity Incentive Plan; options to acquire 16,667 shares vest on 2/14/19; thereafter options to acquire 4,167 shares vest every three months. ( 7 )Stock options granted pursuant to 2016 Equity Incentive Plan; options to acquire 5,000 shares vest on 12/17/18; thereafter options to acquire 1,250 shares vest every three months.

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).

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