| 22. Round | 15/02/2009 | 1. FC Union Berlin | - | Kickers Offenbach | 1:0 | ||||
| 23. Round | 21/02/2009 | Kickers Offenbach | - | Wuppertaler SV | 1:2 | ||||
| 24. Round | 28/02/2009 | Dynamo Dresden | - | Kickers Offenbach | 1:1 | ||||
| 25. Round | 07/03/2009 | Kickers Offenbach | - | Eintracht Braunschweig | 2:0 | ||||
| 21. Round | 10/03/2009 | Wacker Burghausen | - | Kickers Offenbach | 0:0 | ||||
| 26. Round | 15/03/2009 | FC Carl Zeiss Jena | - | Kickers Offenbach | 0:2 |  |
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| 27. Round | 21/03/2009 | Kickers Offenbach | - | VfR Aalen | 2:1 | ||||
| 28. Round | 28/03/2009 | Werder Bremen II | - | Kickers Offenbach | 3:1 | ||||
| 30. Round | 07/04/2009 | Stuttgarter Kickers | - | Kickers Offenbach | 0:1 | ||||
| 31. Round | 11/04/2009 | Kickers Offenbach | - | Fortuna Düsseldorf | 0:2 | ||||
| 33. Round | 25/04/2009 | Kickers Offenbach | - | SV Sandhausen | 0:3 | ||||
| 34. Round | 02/05/2009 | Jahn Regensburg | - | Kickers Offenbach | 1:1 | ||||
| 35. Round | 09/05/2009 | Kickers Offenbach | - | Erzgebirge Aue | 0:0 | ||||
| 36. Round | 13/05/2009 | Rot-Weiß Erfurt | - | Kickers Offenbach | 1:1 |  |
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| 37. Round | 16/05/2009 | Kickers Offenbach | - | Kickers Emden | 0:0 | |
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