| 2. Round | 22/08/2008 | VfL Osnabrück | - | SC Freiburg | 2:2 | ||||
| 3. Round | 29/08/2008 | 1. FSV Mainz 05 | - | VfL Osnabrück | 4:2 | ||||
| 4. Round | 14/09/2008 | VfL Osnabrück | - | FSV Frankfurt | 3:2 |  |
|||
| 5. Round | 21/09/2008 | FC Ingolstadt 04 | - | VfL Osnabrück | 2:1 | ||||
| 7. Round | 05/10/2008 | SpVgg Greuther Fürth | - | VfL Osnabrück | 4:2 | ||||
| 8. Round | 17/10/2008 | VfL Osnabrück | - | Rot-Weiß Oberhausen | 2:1 | ||||
| 9. Round | 26/10/2008 | VfL Osnabrück | - | TSV 1860 München | 0:2 | ||||
| 10. Round | 29/10/2008 | 1. FC Kaiserslautern | - | VfL Osnabrück | 2:0 | ||||
| 11. Round | 02/11/2008 | VfL Osnabrück | - | FC Augsburg | 1:1 | ||||
| 16. Round | 07/12/2008 | Rot Weiss Ahlen | - | VfL Osnabrück | 1:2 | ||||
| 18. Round | 30/01/2009 | VfL Osnabrück | - | FC St. Pauli | 2:2 | ||||
| 19. Round | 06/02/2009 | SC Freiburg | - | VfL Osnabrück | 4:1 |
Brazil