| 1. Round | 09/08/2009 | TSV 1860 München | - | TuS Koblenz | 2:0 |  |
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| 2. Round | 15/08/2009 | Hansa Rostock | - | TSV 1860 München | 2:1 | ||||
| 3. Round | 24/08/2009 | TSV 1860 München | - | Karlsruher SC | 1:3 | |
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| 4. Round | 28/08/2009 | Rot Weiss Ahlen | - | TSV 1860 München | 0:0 | ||||
| 5. Round | 12/09/2009 | TSV 1860 München | - | SpVgg Greuther Fürth | 3:1 | ||||
| 6. Round | 20/09/2009 | Alemannia Aachen | - | TSV 1860 München | 2:0 |  |
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| 7. Round | 27/09/2009 | TSV 1860 München | - | SC Paderborn 07 | 0:0 | ||||
| 8. Round | 04/10/2009 | FC St. Pauli | - | TSV 1860 München | 3:1 | ||||
| 9. Round | 17/10/2009 | TSV 1860 München | - | MSV Duisburg | 3:1 | ||||
| 10. Round | 24/10/2009 | FSV Frankfurt | - | TSV 1860 München | 3:2 | ||||
| 11. Round | 01/11/2009 | TSV 1860 München | - | 1. FC Kaiserslautern | 0:1 | ||||
| 12. Round | 08/11/2009 | Energie Cottbus | - | TSV 1860 München | 1:0 |
USA