| 1. Ronde | 17.08.2008 | Hansa Rostock [A-jun] | - | VfL Osnabrück [A-jun] | 2:0 | ||||
| 2. Ronde | 23.08.2008 | VfL Osnabrück [A-jun] | - | Hertha BSC [A-jun] | 1:2 | ||||
| 3. Ronde | 30.08.2008 | Hamburger SV [A-jun] | - | VfL Osnabrück [A-jun] | 3:2 |  |
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| 5. Ronde | 28.09.2008 | Rot-Weiß Erfurt [A-jun] | - | VfL Osnabrück [A-jun] | 3:0 | ||||
| 6. Ronde | 03.10.2008 | VfL Osnabrück [A-jun] | - | Werder Bremen [A-jun] | 3:0 | ||||
| 7. Ronde | 26.10.2008 | Chemnitzer FC [A-jun] | - | VfL Osnabrück [A-jun] | 1:0 | ||||
| 8. Ronde | 02.11.2008 | VfL Osnabrück [A-jun] | - | Hannover 96 [A-jun] | 1:2 | ||||
| 9. Ronde | 09.11.2008 | Energie Cottbus [A-jun] | - | VfL Osnabrück [A-jun] | 2:0 | ||||
| 13. Ronde | 13.12.2008 | VfL Osnabrück [A-jun] | - | 1. FC Union Berlin [A-jun] | 2:1 | ||||
| 17. Ronde | 08.03.2009 | FC Carl Zeiss Jena [A-jun] | - | VfL Osnabrück [A-jun] | 1:1 | ||||
| 19. Ronde | 22.03.2009 | Werder Bremen [A-jun] | - | VfL Osnabrück [A-jun] | 3:1 |
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