| 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 | ||||
| 3. Round | 29/08/2008 | SV Darmstadt 98 | - | SC Pfullendorf | 0:0 | ||||
| 10. Round | 07/09/2008 | Waldhof Mannheim | - | SV Darmstadt 98 | 2:1 | ||||
| 11. Round | 02/11/2008 | SV Darmstadt 98 | - | Eintracht Frankfurt II | 1:3 | ||||
| 12. Round | 08/11/2008 | SSV Reutlingen | - | SV Darmstadt 98 | 0:2 |  |
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| 15. Round | 29/11/2008 | Viktoria Aschaffenburg | - | SV Darmstadt 98 | 1:1 | ||||
| 22. Round | 13/03/2009 | 1. FC Eintracht Bamberg | - | SV Darmstadt 98 | 2:1 | ||||
| 23. Round | 21/03/2009 | SV Darmstadt 98 | - | TSV 1860 München II | 3:2 | ||||
| 24. Round | 26/03/2009 | Hessen Kassel | - | SV Darmstadt 98 | 3:0 | ||||
| 25. Round | 03/04/2009 | SV Darmstadt 98 | - | SC Freiburg II | 0:0 | ||||
| 28. Round | 03/05/2009 | Eintracht Frankfurt II | - | SV Darmstadt 98 | 2:1 | ||||
| 33. Round | 04/06/2009 | SV Wehen Wiesbaden II | - | SV Darmstadt 98 | 2:0 |  |
Germany