| 21. Round | 06/09/2008 | VfL Osnabrück [Youth B] | - | Hansa Rostock [Youth B] | 2:2 | ||||
| 4. Round | 14/09/2008 | Holstein Kiel [Youth B] | - | VfL Osnabrück [Youth B] | 2:3 |  |
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| 5. Round | 27/09/2008 | VfL Osnabrück [Youth B] | - | FC St. Pauli [Youth B] | 2:1 | ||||
| 14. Round | 11/10/2008 | TeBe Berlin [Youth B] | - | VfL Osnabrück [Youth B] | 1:2 | ||||
| 12. Round | 06/12/2008 | VfL Osnabrück [Youth B] | - | Rot-Weiß Erfurt [Youth B] | 3:1 | ||||
| 13. Round | 14/12/2008 | Werder Bremen [Youth B] | - | VfL Osnabrück [Youth B] | 0:4 | ||||
| 15. Round | 22/02/2009 | VfL Osnabrück [Youth B] | - | Hannover 96 [Youth B] | 1:0 | ||||
| 20. Round | 04/04/2009 | Hertha Zehlendorf [Youth B] | - | VfL Osnabrück [Youth B] | 1:2 | ||||
| 6. Round | 09/04/2009 | Concordia Hamburg [Youth B] | - | VfL Osnabrück [Youth B] | 1:0 | ||||
| 22. Round | 25/04/2009 | Hertha BSC [Youth B] | - | VfL Osnabrück [Youth B] | 5:1 | ||||
| 25. Round | 07/06/2009 | Rot-Weiß Erfurt [Youth B] | - | VfL Osnabrück [Youth B] | 1:0 | ||||
| 26. Round | 14/06/2009 | VfL Osnabrück [Youth B] | - | Werder Bremen [Youth B] | 5:3 |
Germany