| 1. Round | 17/08/2008 | Chemnitzer FC | - | Energie Cottbus II | 1:1 |  |
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| 3. Round | 31/08/2008 | Chemnitzer FC | - | Türkiyemspor Berlin | 1:2 | ||||
| 6. Round | 27/09/2008 | Chemnitzer FC | - | Hannover 96 II | 1:1 | ||||
| 4. Round | 01/10/2008 | FC Oberneuland | - | Chemnitzer FC | 1:0 | ||||
| 7. Round | 08/10/2008 | Holstein Kiel | - | Chemnitzer FC | 2:1 | ||||
| 8. Round | 18/10/2008 | Chemnitzer FC | - | SV Babelsberg 03 | 1:2 | ||||
| 10. Round | 29/10/2008 | Chemnitzer FC | - | Hamburger SV II | 1:0 | ||||
| 12. Round | 08/11/2008 | Chemnitzer FC | - | VfL Wolfsburg II | 1:1 | ||||
| 23. Round | 20/03/2009 | Hannover 96 II | - | Chemnitzer FC | 1:1 | ||||
| 24. Round | 29/03/2009 | Chemnitzer FC | - | Holstein Kiel | 0:1 | ||||
| 30. Round | 13/05/2009 | Chemnitzer FC | - | VFC Plauen | 3:0 | ||||
| 31. Round | 20/05/2009 | Sachsen Leipzig | - | Chemnitzer FC | 0:2 | ||||
| 32. Round | 24/05/2009 | Chemnitzer FC | - | VfB Lübeck | 1:1 | ||||
| 33. Round | 30/05/2009 | SV Wilhelmshaven | - | Chemnitzer FC | 0:1 | ||||
| 34. Round | 07/06/2009 | Chemnitzer FC | - | 1. FC Magdeburg | 1:1 |
Germany