| 2. Jornada | 02.08.2008 | Stuttgarter Kickers | - | Fortuna Düsseldorf | 0:2 | ||||
| 3. Jornada | 17.08.2008 | SpVgg Unterhaching | - | Stuttgarter Kickers | 2:0 | ||||
| 5. Jornada | 30.08.2008 | Jahn Regensburg | - | Stuttgarter Kickers | 1:1 | ||||
| 6. Jornada | 13.09.2008 | Stuttgarter Kickers | - | Erzgebirge Aue | 1:2 | ||||
| 7. Jornada | 20.09.2008 | Rot-Weiß Erfurt | - | Stuttgarter Kickers | 3:2 |  |
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| 11. Jornada | 25.10.2008 | Kickers Offenbach | - | Stuttgarter Kickers | 4:0 | ||||
| 12. Jornada | 28.10.2008 | Stuttgarter Kickers | - | 1. FC Union Berlin | 2:2 | ||||
| 13. Jornada | 31.10.2008 | Wuppertaler SV | - | Stuttgarter Kickers | 3:3 | |
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| 14. Jornada | 08.11.2008 | Stuttgarter Kickers | - | Dynamo Dresden | 2:1 | ||||
| 15. Jornada | 15.11.2008 | Eintracht Braunschweig | - | Stuttgarter Kickers | 1:1 | ||||
| 18. Jornada | 07.12.2008 | Stuttgarter Kickers | - | Werder Bremen II | 3:2 | ||||
| 19. Jornada | 13.12.2008 | SC Paderborn 07 | - | Stuttgarter Kickers | 2:0 | ||||
| 21. Jornada | 05.02.2009 | Fortuna Düsseldorf | - | Stuttgarter Kickers | 2:0 | ||||
| 27. Jornada | 21.03.2009 | Kickers Emden | - | Stuttgarter Kickers | 0:1 |
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