SEC Contract Filing

Filing Date: 2023-02-21

Document Content:
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<TYPE>EX-10.1
<SEQUENCE>3
<FILENAME>ex10-1.htm
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<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: right"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt"><B>Exhibit
10.1</B></FONT></P>

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<P STYLE="text-align: right; font: 10pt Times New Roman, Times, Serif; margin: 0pt 0"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt"><B>EXECUTION
VERSION</B></FONT></P>

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<P STYLE="font: bold 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: center"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt">AMENDMENT
AND EXCHANGE AGREEMENT</FONT></P>

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<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: justify; text-indent: 1in"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt">This
Amendment and Exchange Agreement (the &ldquo;<B>Agreement</B>&rdquo;) is entered into as of the 20<SUP>th</SUP> day of February, 2023,
by and among Gaucho Group Holdings, Inc., a Delaware corporation (the &ldquo;<B>Company</B>&rdquo;) and the investor signatory hereto
(the &ldquo;<B>Holder</B>&rdquo;), with reference to the following facts:</FONT></P>

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<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt; text-align: justify; text-indent: 1in"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt">A.
Prior to the date hereof, pursuant to that Securities Purchase Agreement, dated as of November 3, 2021, by and between the Company and
the investors (including the Holder, the &ldquo;<B>Holders</B>&rdquo;) (as the same has been amended, restated, amended and restated,
supplemented or otherwise modified prior to the date hereof, the &ldquo;<B>Securities Purchase Agreement</B>&rdquo;) and the Registration
Rights Agreement by and between the Company and the Holders dated November 9, 2021 (as the same has been amended, restated, amended and
restated, supplemented or otherwise modified prior to the date hereof, the &ldquo;<B>Registration Rights Agreement</B>&rdquo;), the Company
issued to the Holders certain senior secured convertible notes (as the same has been amended, restated, amended and restated, supplemented
or otherwise modified prior to the date hereof, each, an &ldquo;<B>Existing Note</B>&rdquo; and together with the Securities Purchase
Agreement, the &ldquo;<B>Existing Note Documents</B>&rdquo;). Capitalized terms used but not otherwise defined herein shall have the
meanings as set forth in the Securities Purchase Agreement (as amended hereby) or, as the context may require, the Existing Notes.</FONT></P>

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<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt; text-align: justify; text-indent: 1in"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt">B.
As of the date of this Agreement, the Holder is the holder of such aggregate principal amount of Existing Notes as set forth on the signature
page of the Holder attached hereto and has not assigned, transferred or exchanged any of its Existing Notes.</FONT></P>

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<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt; text-align: justify; text-indent: 1in"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt">C.
The Company and the Holder desire to amend and waive certain provisions of the Existing Note Documents and exchange (the &ldquo;<B>Exchange</B>&rdquo;
or the &ldquo;<B>Transaction</B>&rdquo;) $100 in aggregate principal amount of the Existing Note (the &ldquo;<B>Exchange Note</B>&rdquo;),
on the basis and subject to the terms and conditions set forth in this Agreement, for a warrant, in the form attached hereto as <B><U>Exhibit
A </U></B>(the &ldquo;<B>New Warrant</B>&rdquo;), exercisable into such aggregate number of shares of Common Stock of the Company as
set forth on the signature page of the Holder attached hereto (the &ldquo;<B>New Warrant Shares</B>&rdquo;, and together with the New
Warrant, collectively, the &ldquo;<B>New Securities</B>&rdquo;).</FONT></P>

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<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt; text-align: justify; text-indent: 1in"><FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt">D.
The New Warrant and this Agreement and such other documents and certificates related thereto are collectively referred to herein as the
&ldquo;<B>Exchange Documents</B>&rdquo;.</FONT></P>

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