| 1. Round | 17/08/2008 | SC Freiburg | - | TSV 1860 München | 2:1 |  |
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| 2. Round | 22/08/2008 | VfL Osnabrück | - | SC Freiburg | 2:2 | ||||
| 4. Round | 14/09/2008 | FC Augsburg | - | SC Freiburg | 1:3 | ||||
| 5. Round | 21/09/2008 | SC Freiburg | - | SV Wehen Wiesbaden | 5:0 | ||||
| 6. Round | 28/09/2008 | Alemannia Aachen | - | SC Freiburg | 1:0 |  |
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| 11. Round | 02/11/2008 | FC Ingolstadt 04 | - | SC Freiburg | 4:0 | ||||
| 26. Round | 06/04/2009 | SC Freiburg | - | Rot Weiss Ahlen | 1:1 | ||||
| 34. Round | 24/05/2009 | SC Freiburg | - | 1. FC Kaiserslautern | 4:3 |
Germany