| 1. Round | 15/08/2008 | Waldhof Mannheim | - | TSV 1860 München II | 1:4 |  |
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| 2. Round | 22/08/2008 | TSV 1860 München II | - | Eintracht Frankfurt II | 0:1 | |
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| 3. Round | 29/08/2008 | SSV Reutlingen | - | TSV 1860 München II | 1:1 | ||||
| 4. Round | 12/09/2008 | TSV 1860 München II | - | 1. FC Heidenheim 1846 | 0:3 | |
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| 5. Round | 19/09/2008 | TSV Großbardorf | - | TSV 1860 München II | 3:1 | |
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| 6. Round | 27/09/2008 | TSV 1860 München II | - | SV Darmstadt 98 | 0:0 | ||||
| 7. Round | 04/10/2008 | SV Wehen Wiesbaden II | - | TSV 1860 München II | 0:0 | |
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| 9. Round | 25/10/2008 | Karlsruher SC II | - | TSV 1860 München II | 1:3 | ||||
| 10. Round | 28/10/2008 | TSV 1860 München II | - | 1. FC Nürnberg II | 0:1 | |
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| 11. Round | 02/11/2008 | SC Pfullendorf | - | TSV 1860 München II | 2:0 | ||||
| 12. Round | 07/11/2008 | TSV 1860 München II | - | SSV Ulm 1846 | 2:2 |  |
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| 13. Round | 15/11/2008 | 1. FC Eintracht Bamberg | - | TSV 1860 München II | 1:2 | |
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| 15. Round | 28/11/2008 | TSV 1860 München II | - | Hessen Kassel | 2:1 | ||||
| 14. Round | 02/12/2008 | TSV 1860 München II | - | Viktoria Aschaffenburg | 3:0 | |
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| 16. Round | 06/12/2008 | SC Freiburg II | - | TSV 1860 München II | 1:3 |
Germany