| 3. Round | 16/08/2008 | Erzgebirge Aue | - | VfR Aalen | 0:0 | ||||
| 4. Round | 23/08/2008 | VfR Aalen | - | Rot-Weiß Erfurt | 0:2 | ||||
| 35. Round | 09/05/2009 | VfR Aalen | - | SC Paderborn 07 | 3:3 | ||||
| 36. Round | 12/05/2009 | Stuttgarter Kickers | - | VfR Aalen | 1:4 | ||||
| 37. Round | 16/05/2009 | VfR Aalen | - | Fortuna Düsseldorf | 1:2 | ||||
| 38. Round | 23/05/2009 | SpVgg Unterhaching | - | VfR Aalen | 2:1 |  |
Germany