FORM 4 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
or Section 30(h) of the Investment Company Act of 1940
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Check this box if no longer subject to Section 16. Form 4 or Form 5 obligations may continue. See Instruction 1(b).
1. Name and Address of Reporting Person *
Cannon Reuben

(Last) (First) (Middle)
280 S. BEVERLY DRIVE #208

(Street)
BEVERLY HILLS, CA 90212

(City) (State) (Zip)
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
Officer (give title below) Other (specify below)
3. Date of Earliest Transaction (Month/Day/Year)
06/24/2022
4. If Amendment, Date of Original Filed (Month/Day/Year)
6. Individual or Joint/Group Filing (Check Applicable Line)
X Form filed by One Reporting Person
Form filed by More than One Reporting Person
Table I - Non-Derivative Securities Acquired, Disposed of, or Beneficially Owned
1. Title of Security (Instr. 3) 2. Transaction Date (Month/Day/Year) 2A. Deemed Execution Date, if any (Month/Day/Year) 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) 06/24/2022   A   10,033 A $ 0.625 126,876 D  
Common Stock               1,960 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 (Month/Day/Year) 3A. Deemed Execution Date, if any (Month/Day/Year) 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 (Month/Day/Year) 7. Title and Amount of Securities Underlying Derivative Security (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: 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
Restricted Stock Unit $ 0.625 06/24/2022   A   1,433     (3) 12/18/2023 Common Stock 1,433 $ 0.625 1,433 D  
Warrants (4) $ 6             02/19/2021 08/19/2022 Common Stock 3,333   3,333 D  
Stock Option $ 8.09               (5) 09/20/2023 Common Stock 1,000   1,000 D  
Stock Option $ 9.08               (6) 09/28/2025 Common Stock 6,667   6,667 D  
Explanation of Responses:
1. Acquired in connection with the conversion of outstanding options of Gaucho Group, Inc.
2. Held by Reuben Cannon Productions, controlled by Mr. Cannon.
3. Restricted stock units issued pursuant to Gaucho's 2018 Equity Incentive Plan; 717 shares vest on 9/18/22 with the remainder vesting on 12/18/22.
4. Purchased pursuant to a public offering of Units at a price of $6.00 per Unit, with each Unit consisting of one share of common stock and one common stock purchase warrant; each warrant has an exercise price equal to 100% of the offering price.
5. Options granted pursuant to 2018 Equity Incentive Plan; options to acquire 250 shares vest on 9/20/19; options to acquire 63 shares vest on 12/20/19; thereafter options to acquire 62 shares vest every three months.
6. Options granted pursuant to Gaucho's 2018 Equity Incentive Plan; options to acquire 1,667 shares vest on 9/28/21; thereafter options to acquire 417 shares vest every three months.
/s/ Reuben Cannon 06/24/2022
** Signature of Reporting Person Date
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* 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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