| 1. Round | 15/08/2008 | Hertha BSC II | - | VfL Wolfsburg II | 0:2 | ||||
| 2. Round | 22/08/2008 | VFC Plauen | - | Hertha BSC II | 2:2 | ||||
| 3. Round | 31/08/2008 | Hertha BSC II | - | Sachsen Leipzig | 2:1 | ||||
| 5. Round | 07/09/2008 | Hertha BSC II | - | SV Wilhelmshaven | 1:3 |  |
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| 6. Round | 26/09/2008 | 1. FC Magdeburg | - | Hertha BSC II | 2:0 | ||||
| 7. Round | 04/10/2008 | Hertha BSC II | - | Energie Cottbus II | 1:0 | ||||
| 10. Round | 29/10/2008 | FC Oberneuland | - | Hertha BSC II | 2:0 | ||||
| 11. Round | 01/11/2008 | Hertha BSC II | - | Chemnitzer FC | 1:2 | ||||
| 12. Round | 08/11/2008 | Hannover 96 II | - | Hertha BSC II | 4:2 | |
Germany