| 2. Round | 22/08/2008 | VFC Plauen | - | Hertha BSC II | 2:2 | ||||
| 3. Round | 31/08/2008 | Hertha BSC II | - | Sachsen Leipzig | 2:1 |  |
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| 4. Round | 13/09/2008 | VfB Lübeck | - | Hertha BSC II | 4:0 | |
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| 7. Round | 04/10/2008 | Hertha BSC II | - | Energie Cottbus II | 1:0 | ||||
| 9. Round | 25/10/2008 | Hertha BSC II | - | Türkiyemspor Berlin | 2:1 | ||||
| 10. Round | 29/10/2008 | FC Oberneuland | - | Hertha BSC II | 2:0 | ||||
| 11. Round | 01/11/2008 | Hertha BSC II | - | Chemnitzer FC | 1:2 |
Russia