| 1. Round | 17/08/2008 | VfL Osnabrück [Youth B] | - | TeBe Berlin [Youth B] | 1:4 | ||||
| 10. Round | 16/11/2008 | Hamburger SV [Youth B] | - | VfL Osnabrück [Youth B] | 0:1 | ||||
| 11. Round | 30/11/2008 | VfL Wolfsburg [Youth B] | - | VfL Osnabrück [Youth B] | 4:0 | ||||
| 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 | ||||
| 18. Round | 15/03/2009 | FC St. Pauli [Youth B] | - | VfL Osnabrück [Youth B] | 0:3 | ||||
| 22. Round | 25/04/2009 | Hertha BSC [Youth B] | - | VfL Osnabrück [Youth B] | 5:1 |  |
|||
| 23. Round | 17/05/2009 | VfL Osnabrück [Youth B] | - | Hamburger SV [Youth B] | 1:3 | ||||
| 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