| 2. Round | 23/08/2008 | Holstein Kiel [Youth B] | - | Hertha BSC [Youth B] | 0:5 | ||||
| 3. Round | 31/08/2008 | Hamburger SV [Youth B] | - | Holstein Kiel [Youth B] | 4:0 | ||||
| 6. Round | 05/10/2008 | Holstein Kiel [Youth B] | - | Werder Bremen [Youth B] | 2:3 | ||||
| 14. Round | 11/10/2008 | Holstein Kiel [Youth B] | - | Hansa Rostock [Youth B] | 2:0 | ||||
| 9. Round | 09/11/2008 | Energie Cottbus [Youth B] | - | Holstein Kiel [Youth B] | 3:1 | ||||
| 13. Round | 14/12/2008 | Holstein Kiel [Youth B] | - | Hertha Zehlendorf [Youth B] | 2:2 |  |
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| 15. Round | 22/02/2009 | Hertha BSC [Youth B] | - | Holstein Kiel [Youth B] | 9:0 | ||||
| 19. Round | 22/03/2009 | Werder Bremen [Youth B] | - | Holstein Kiel [Youth B] | 5:1 | ||||
| 24. Round | 24/05/2009 | FC St. Pauli [Youth B] | - | Holstein Kiel [Youth B] | 6:1 |
Germany