| 1. Round | 07/08/2009 | TSV 1860 München II | - | Hessen Kassel | 3:3 |  |
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| 4. Round | 29/08/2009 | Hessen Kassel | - | SG Sonnenhof Großaspach | 3:0 | ||||
| 5. Round | 02/09/2009 | SpVgg Greuther Fürth II | - | Hessen Kassel | 1:2 | ||||
| 6. Round | 06/09/2009 | Hessen Kassel | - | SC Pfullendorf | 5:2 | ||||
| 8. Round | 20/09/2009 | Hessen Kassel | - | Eintracht Frankfurt II | 1:0 | |
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| 9. Round | 26/09/2009 | 1. FC Eintracht Bamberg | - | Hessen Kassel | 3:1 | ||||
| 11. Round | 17/10/2009 | SSV Reutlingen | - | Hessen Kassel | 1:1 | ||||
| 13. Round | 30/10/2009 | Hessen Kassel | - | VfR Aalen | 0:1 | |
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| 14. Round | 07/11/2009 | 1. FC Nürnberg II | - | Hessen Kassel | 1:1 | ||||
| 15. Round | 21/11/2009 | Hessen Kassel | - | Stuttgarter Kickers | 0:0 | |
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| 16. Round | 28/11/2009 | SV Wehen Wiesbaden II | - | Hessen Kassel | 1:2 | ||||
| 17. Round | 04/12/2009 | Hessen Kassel | - | SpVgg Weiden | 3:1 | ||||
| 19. Round | 12/12/2009 | SV Darmstadt 98 | - | Hessen Kassel | 2:3 |
Germany