| 1. Round | 25/07/2009 | Dynamo Dresden | - | VfB Stuttgart II | 0:1 | ||||
| 2. Round | 29/07/2009 | VfB Stuttgart II | - | 1. FC Heidenheim 1846 | 1:1 | ||||
| 3. Round | 08/08/2009 | Wuppertaler SV | - | VfB Stuttgart II | 0:3 | ||||
| 6. Round | 29/08/2009 | SV Sandhausen | - | VfB Stuttgart II | 2:1 | ||||
| 7. Round | 01/09/2009 | VfB Stuttgart II | - | Bayern München II | 2:4 | ||||
| 8. Round | 05/09/2009 | Erzgebirge Aue | - | VfB Stuttgart II | 1:0 |  |
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| 9. Round | 12/09/2009 | VfB Stuttgart II | - | Rot-Weiß Erfurt | 3:1 |  |
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| 10. Round | 19/09/2009 | VfL Osnabrück | - | VfB Stuttgart II | 0:1 | ||||
| 11. Round | 26/09/2009 | VfB Stuttgart II | - | Borussia Dortmund II | 2:1 | ||||
| 12. Round | 02/10/2009 | Holstein Kiel | - | VfB Stuttgart II | 2:0 | ||||
| 16. Round | 07/11/2009 | Kickers Offenbach | - | VfB Stuttgart II | 2:0 | ||||
| 17. Round | 20/11/2009 | VfB Stuttgart II | - | FC Ingolstadt 04 | 2:4 | |
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| 18. Round | 28/11/2009 | SpVgg Unterhaching | - | VfB Stuttgart II | 1:0 | ||||
| 19. Round | 04/12/2009 | VfB Stuttgart II | - | FC Carl Zeiss Jena | 0:1 | ||||
| 20. Round | 12/12/2009 | VfB Stuttgart II | - | Dynamo Dresden | 2:2 |
Germany