| 1. Round | 17/08/2008 | SC Freiburg | - | TSV 1860 München | 2:1 | ||||
| 2. Round | 24/08/2008 | TSV 1860 München | - | 1. FSV Mainz 05 | 1:2 | ||||
| 3. Round | 31/08/2008 | Rot Weiss Ahlen | - | TSV 1860 München | 2:1 |  |
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| 4. Round | 15/09/2008 | TSV 1860 München | - | MSV Duisburg | 2:0 | |
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| 5. Round | 19/09/2008 | FC St. Pauli | - | TSV 1860 München | 1:0 | ||||
| 6. Round | 28/09/2008 | TSV 1860 München | - | FC Ingolstadt 04 | 1:1 | ||||
| 7. Round | 03/10/2008 | FSV Frankfurt | - | TSV 1860 München | 0:3 | ||||
| 8. Round | 19/10/2008 | TSV 1860 München | - | SpVgg Greuther Fürth | 3:1 | ||||
| 9. Round | 26/10/2008 | VfL Osnabrück | - | TSV 1860 München | 0:2 | ||||
| 13. Round | 14/11/2008 | TSV 1860 München | - | FC Augsburg | 0:1 | ||||
| 14. Round | 24/11/2008 | Hansa Rostock | - | TSV 1860 München | 0:1 | ||||
| 16. Round | 05/12/2008 | Alemannia Aachen | - | TSV 1860 München | 2:0 |
Germany
Italy