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 September 30, 2021 OR ☐ TRANSITION REPORT UNDER SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from _____________ to ___________________. Commission file number: 000-55209 Gaucho Group Holdings, Inc. (Exact name of registrant as specified in its charter) Delaware 52-215 ...

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 June 30, 2021 OR ☐ TRANSITION REPORT UNDER SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from _____________ to ___________________. Commission file number: 000-55209 Gaucho Group Holdings, Inc. (Exact name of registrant as specified in its charter) (State or other juri ...

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D. C. 20549 [X] QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended March 31, 2021 OR [ ] TRANSITION REPORT UNDER SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from _____________ to ___________________. Commission file number: 000-55209 Gaucho Group Holdings, Inc. (Exact name of registrant as specified in its charter) | Delaware | 52-2158952 | ...

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 10-K (Mark one) [X] ANNUAL REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the Fiscal Year Ended December 31, 2020 [ ] 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: 000-55209 Gaucho Group Holdings, Inc. (Exact Name of Registrant as Specified in Its Charter) | Delawa ...

[PART I FINANCIAL INFORMATION](index=3&type=section&id=PART%20I%20FINANCIAL%20INFORMATION) [Financial Statements](index=3&type=section&id=ITEM%201.%20Financial%20Statements) The company's financial statements for the period ended September 30, 2020, reflect a challenging financial position with significant deficits and net losses, raising substantial doubt about its going concern ability [Condensed Consolidated Balance Sheets](index=3&type=section&id=Condensed%20Consolidated%20Balance%20Sheets) As of September 30, 2020, the company reported total assets of $6.88 million and total liabilities of $7.37 million, resulting in a $9.50 million stockholders' deficiency and a $3.45 million working capital deficit Condensed Consolidated Balance Sheet Highlights (unaudited) | Balance Sheet Items | Sep 30, 2020 (unaudited, in USD) | Dec 31, 2019 (in USD) | | :--- | :--- | :--- | | **Assets** | | | | Cash | $1,210,668 | $40,378 | | Total Current Assets | $3,566,856 | $2,428,747 | | Total Assets | $6,882,950 | $5,920,360 | | **Liabilities & Stockholders' Deficiency** | | | | Total Current Liabilities | $7,018,676 | $5,737,953 | | Total Liabilities | $7,370,082 | $5,920,934 | | Total Stockholders' Deficiency | $(9,497,956) | $(9,027,398) | [Condensed Consolidated Statements of Operations](index=5&type=section&id=Condensed%20Consolidated%20Statements%20of%20Operations) For the nine months ended September 30, 2020, sales decreased by 49% to $474,546, resulting in a net loss of $3.74 million, an improvement from the prior year due to reduced operating expenses Statement of Operations Summary (unaudited) | Metric | Nine Months Ended Sep 30, 2020 (unaudited, in USD) | Nine Months Ended Sep 30, 2019 (in USD) | | :--- | :--- | :--- | | Sales | $474,546 | $940,459 | | Gross Loss | $(97,075) | $(7,251) | | Loss from Operations | $(3,708,170) | $(4,669,929) | | Net Loss | $(3,736,028) | $(4,819,585) | | Net Loss Attributable to Common Stockholders | $(4,147,890) | $(5,203,381) | | Net Loss per Common Share | $(0.07) | $(0.10) | [Condensed Consolidated Statements of Cash Flows](index=9&type=section&id=Condensed%20Consolidated%20Statements%20of%20Cash%20Flows) For the nine months ended September 30, 2020, operations used $3.68 million in cash, offset by $4.49 million from financing activities, leading to a net cash increase of $1.17 million and an ending balance of $1.21 million Cash Flow Summary (unaudited) | Cash Flow Activity | Nine Months Ended Sep 30, 2020 (unaudited, in USD) | Nine Months Ended Sep 30, 2019 (in USD) | | :--- | :--- | :--- | | Net Cash Used in Operating Activities | $(3,682,663) | $(5,136,444) | | Net Cash Used in Investing Activities | $(39,859) | $(147,944) | | Net Cash Provided by Financing Activities | $4,492,126 | $5,138,085 | | Net Increase in Cash | $1,170,290 | $449,884 | | **Cash at End of Period** | **$1,210,668** | **$508,372** | - Non-cash financing activities for the nine months ended September 30, 2020, included the conversion of **$1,260,314** in debt and interest to equity and the issuance of **$140,600** in common stock for a subscription receivable[29](index=29&type=chunk) [Notes to Unaudited Condensed Consolidated Financial Statements](index=11&type=section&id=Notes%20to%20Unaudited%20Condensed%20Consolidated%20Financial%20Statements) The notes highlight a going concern warning due to significant losses and deficits, detail the impact of the COVID-19 pandemic on operations across its Real Estate, Fashion, and Corporate segments, and disclose various debt defaults and equity transactions - The company's financial condition raises substantial doubt about its ability to continue as a going concern, reporting a working capital deficit of **$3.45 million**, a net loss of **$3.74 million**, and **$3.68 million** cash used in operations for the nine-month period[34](index=34&type=chunk)[35](index=35&type=chunk) - The COVID-19 pandemic caused temporary closures of the company's hospitality and corporate operations, leading to cost-cutting measures including lease termination and salary reductions[36](index=36&type=chunk) - The company operates in **Real Estate Development**, **Fashion**, and **Corporate** segments; for the nine months ended September 30, 2020, Real Estate generated **$473,797** in revenue with an operating loss of **$894,842**, while Fashion had **$749** in revenue and an operating loss of **$723,921**[43](index=43&type=chunk)[124](index=124&type=chunk)[126](index=126&type=chunk) - Subsequent to quarter-end, the company issued common stock to settle 401(k) obligations, pay for consulting services, and pay **$1.63 million** in accrued preferred stock dividends, also selling an additional **$75,000** in Units[131](index=131&type=chunk)[133](index=133&type=chunk)[134](index=134&type=chunk) [Management's Discussion and Analysis of Financial Condition and Results of Operations](index=29&type=section&id=ITEM%202.%20Management%27s%20Discussion%20and%20Analysis%20of%20Financial%20Condition%20and%20Results%20of%20Operations) Management discusses the company's financial performance, liquidity challenges, and the significant impact of the COVID-19 pandemic, emphasizing substantial doubt about its going concern ability due to deficits and reliance on continuous financing [Recent Developments and Trends](index=29&type=section&id=Recent%20Developments%20and%20Trends) The company's operations were significantly impacted by the COVID-19 pandemic, leading to temporary closures, cost-cutting measures like lease termination and salary reductions, and the development of an e-commerce platform - The company mitigated COVID-19 financial impact by closing corporate and hospitality operations, terminating its New York lease, and implementing salary reductions[144](index=144&type=chunk) [Consolidated Results of Operations](index=30&type=section&id=Consolidated%20Results%20of%20Operations) For the nine months ended September 30, 2020, revenues decreased by 49% to $475,000, while a 23% reduction in general and administrative expenses helped narrow the net loss to $3.7 million from $4.8 million in 2019 Comparison of Operations for the Three Months Ended September 30 | Metric | 2020 (in USD) | 2019 (in USD) | Change (%) | | :--- | :--- | :--- | :--- | | Revenues | $60,000 | $231,000 | -74% | | Gross Loss | $(21,000) | $(86,000) | -76% | | General & Administrative Expenses | $860,000 | $1,411,000 | -39% | | Net Loss | $(900,000) | $(1,400,000) | -36% | Comparison of Operations for the Nine Months Ended September 30 | Metric | 2020 (in USD) | 2019 (in USD) | Change (%) | | :--- | :--- | :--- | :--- | | Revenues | $475,000 | $940,000 | -49% | | Gross Loss | $(97,000) | $(7,000) | +1,286% | | General & Administrative Expenses | $3,342,000 | $4,340,000 | -23% | | Net Loss | $(3,700,000) | $(4,800,000) | -23% | [Liquidity and Capital Resources](index=33&type=section&id=Liquidity%20and%20Capital%20Resources) The company faces severe liquidity constraints with a $3.45 million working capital deficiency, relying on continuous financing, and management warns that current cash is only sufficient for month-to-month operations, necessitating additional capital for survival Liquidity Metrics | Metric | Sep 30, 2020 (in USD) | Dec 31, 2019 (in USD) | | :--- | :--- | :--- | | Cash | $1,210,668 | $40,378 | | Working Capital (Deficiency) | $(3,451,820) | $(3,309,206) | - During the nine months ended September 30, 2020, the company relied on financing, securing **$3.2 million** from convertible debt, **$1.2 million** from common stock offerings, and approximately **$336,000** from government loans[174](index=174&type=chunk) - Management explicitly states substantial doubt about the company's going concern ability, noting that current cash reserves only support month-to-month operations[181](index=181&type=chunk)[183](index=183&type=chunk) [Quantitative and Qualitative Disclosures About Market Risk](index=34&type=section&id=ITEM%203.%20Quantitative%20and%20Qualitative%20Disclosures%20About%20Market%20Risk) As a smaller reporting company, the company is not required to provide quantitative and qualitative disclosures about market risk - As a "smaller reporting company," the company is exempt from providing the information required by this item[187](index=187&type=chunk) [Controls and Procedures](index=35&type=section&id=ITEM%204.%20Controls%20and%20Procedures) Management concluded that the company's disclosure controls and procedures were effective as of September 30, 2020, with no material changes to internal control over financial reporting during the quarter - The Principal Executive Officer and Principal Financial Officer concluded the company's disclosure controls and procedures were effective as of September 30, 2020[189](index=189&type=chunk) - No material changes to internal control over financial reporting occurred during the quarter[190](index=190&type=chunk) [PART II OTHER INFORMATION](index=36&type=section&id=PART%20II%20OTHER%20INFORMATION) [Legal Proceedings](index=36&type=section&id=ITEM%201.%20Legal%20Proceedings) The company is not involved in any litigation expected to have a material adverse effect on its financial condition, results of operations, or cash flows - The company is subject to incidental litigation but does not anticipate any pending claims will have a material adverse effect[194](index=194&type=chunk) [Risk Factors](index=36&type=section&id=ITEM%201A.%20Risk%20Factors) As a smaller reporting company, the company updates its COVID-19 related risks, highlighting significant business disruptions including lease termination, production delays, and reduced marketing, all negatively impacting sales - The company faces significant business disruption from the COVID-19 pandemic, leading to early termination of its New York office lease[196](index=196&type=chunk) - Significant delays in product development and shipping from manufacturing partners, some of whom closed permanently, forced the company to seek new vendors[198](index=198&type=chunk) - Disruptions in order fulfillment led to reduced email marketing, significantly decreasing web traffic and sales[199](index=199&type=chunk) [Unregistered Sales of Equity Securities and Use of Proceeds](index=36&type=section&id=ITEM%202.%20Unregistered%20Sales%20of%20Equity%20Securities%20and%20Use%20of%20Proceeds) During 2020, the company conducted multiple private placements of unsecured convertible promissory notes and units to accredited investors under Section 4(a)(2) and Rule 506(b) of Regulation D - The company sold unsecured convertible promissory notes to accredited investors through private placements exempt from registration under Rule 506(b)[201](index=201&type=chunk) - The company sold "New Convertible Notes" totaling **$1,259,000** that mandatorily converted into Units at **$0.34** per Unit in late August and early September 2020[205](index=205&type=chunk) [Defaults Upon Senior Securities](index=37&type=section&id=ITEM%203.%20Defaults%20Upon%20Senior%20Securities) The company is in default on several senior securities, including 2017 and 2018 bank loans, 2017 Notes totaling approximately $1.4 million, and a $100,000 subsidiary note, all now payable on demand - The company has defaulted on multiple loans, including the 2017 and 2018 Loans, which are now payable on demand[206](index=206&type=chunk)[207](index=207&type=chunk) - As of September 30, 2020, 2017 convertible promissory notes with **$1,170,354** principal and **$237,521** interest are past due, payable on demand, and no longer convertible[208](index=208&type=chunk) - A convertible note from the company's subsidiary GGI, with **$100,000** principal and **$11,508** interest, is past due and payable on demand[209](index=209&type=chunk) [Mine Safety Disclosures](index=37&type=section&id=ITEM%204.%20Mine%20Safety%20Disclosures) This item is not applicable to the company - Not applicable[210](index=210&type=chunk) [Other Information](index=37&type=section&id=ITEM%205.%20Other%20Information) Subsequent to the reporting period, in October 2020, the company continued financing activities by selling $75,000 in Units and issuing common stock to settle 401(k) obligations, pay for consulting services, and fulfill advisory agreements - Between October 14 and October 29, 2020, the company sold an additional **$75,000** in Units to accredited investors[211](index=211&type=chunk) - On October 3, 2020, the company issued **142,597 shares** of common stock to settle its 2019 401(k) profit-sharing plan obligations[212](index=212&type=chunk) - In October 2020, the company issued **125,000 shares** for consulting services and **1,011,643 shares** as part of an advisory agreement with Kingswood Capital Markets[213](index=213&type=chunk)[214](index=214&type=chunk) [Exhibits](index=39&type=section&id=ITEM%206.%20Exhibits) This section lists all exhibits filed as part of the Form 10-Q, including corporate governance documents, securities designations, material contracts, and Sarbanes-Oxley certifications

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D. C. 20549 For the quarterly period ended June 30, 2020 OR [ ] TRANSITION REPORT UNDER SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 FORM 10-Q For the transition period from _____________ to ___________________. [X] QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 8 Union Square 2A New York, NY 10003 (Address of principal executive offices) 212-739-7700 (Registrant's telephone number, including ...

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 March 31, 2020 OR [ ] TRANSITION REPORT UNDER SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from _____________ to ___________________. Commission file number: 000-55209 Gaucho Group Holdings, Inc. (Exact name of registrant as specified in its charter) Delaware 52-215 ...

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 10-K (Mark one) [X] ANNUAL REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the Fiscal Year Ended December 31, 2019 [ ] 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: 000-55209 Gaucho Group Holdings, Inc. (Exact Name of Registrant as Specified in Its Charter) | Delawa ...

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 September 30, 2019 OR [ ] TRANSITION REPORT UNDER SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from _____________ to ___________________. Commission file number: 000-55209 Gaucho Group Holdings, Inc. (Exact name of registrant as specified in its charter) Delaware 52 ...

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 June 30, 2019 OR [ ] TRANSITION REPORT UNDER SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from _____________ to ___________________. Commission file number: 000-55209 Gaucho Group Holdings, Inc. (Exact name of registrant as specified in its charter) Delaware 52-2158 ...