| 1. Round | 16/08/2008 | SV Darmstadt 98 | - | Karlsruher SC II | 1:4 | ||||
| 2. Round | 23/08/2008 | 1. FC Nürnberg II | - | SV Darmstadt 98 | 4:0 |  |
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| 10. Round | 07/09/2008 | Waldhof Mannheim | - | SV Darmstadt 98 | 2:1 | ||||
| 4. Round | 13/09/2008 | SSV Ulm 1846 | - | SV Darmstadt 98 | 1:0 | ||||
| 5. Round | 19/09/2008 | SV Darmstadt 98 | - | 1. FC Eintracht Bamberg | 5:2 |  |
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| 7. Round | 04/10/2008 | SV Darmstadt 98 | - | Hessen Kassel | 2:2 |  |
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| 15. Round | 29/11/2008 | Viktoria Aschaffenburg | - | SV Darmstadt 98 | 1:1 | ||||
| 17. Round | 17/12/2008 | SpVgg Unterhaching II | - | SV Darmstadt 98 | 1:3 | ||||
| 18. Round | 20/12/2008 | Karlsruher SC II | - | SV Darmstadt 98 | 0:2 | ||||
| 23. Round | 21/03/2009 | SV Darmstadt 98 | - | TSV 1860 München II | 3:2 | ||||
| 33. Round | 04/06/2009 | SV Wehen Wiesbaden II | - | SV Darmstadt 98 | 2:0 | ||||
| 34. Round | 06/06/2009 | SV Darmstadt 98 | - | SpVgg Unterhaching II | 6:3 |
Germany