| 1. Round | 19/07/2019 | TSV 1860 München | - | Preußen Münster | 1:1 | ||||
| 2. Round | 27/07/2019 | Eintracht Braunschweig | - | TSV 1860 München | 2:1 | ||||
| 3. Round | 31/07/2019 | TSV 1860 München | - | FSV Zwickau | 3:0 | ||||
| 4. Round | 05/08/2019 | Waldhof Mannheim | - | TSV 1860 München | 4:0 | ||||
| 5. Round | 17/08/2019 | TSV 1860 München | - | SV Meppen | 0:0 | ||||
| 6. Round | 24/08/2019 | 1. FC Magdeburg | - | TSV 1860 München | 5:1 | ||||
| 7. Round | 30/08/2019 | Chemnitzer FC | - | TSV 1860 München | 0:1 | ||||
| 8. Round | 14/09/2019 | TSV 1860 München | - | FC Carl Zeiss Jena | 3:1 | ||||
| 9. Round | 21/09/2019 | MSV Duisburg | - | TSV 1860 München | 2:1 | ||||
| 10. Round | 28/09/2019 | TSV 1860 München | - | 1. FC Kaiserslautern | 3:1 | ||||
| 11. Round | 07/10/2019 | Würzburger Kickers | - | TSV 1860 München | 2:1 | ||||
| 12. Round | 19/10/2019 | TSV 1860 München | - | KFC Uerdingen 05 | 0:1 |  |
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| 13. Round | 26/10/2019 | Hansa Rostock | - | TSV 1860 München | 2:1 | ||||
| 22. Round | 02/02/2020 | FSV Zwickau | - | TSV 1860 München | 2:2 | |
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| 37. Round | 01/07/2020 | SG Sonnenhof Großaspach | - | TSV 1860 München | 2:4 | |
Germany