| 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 | ||||
| 4. Round | 16/08/2009 | VfB Stuttgart II | - | Jahn Regensburg | 2:3 | ||||
| 5. Round | 23/08/2009 | VfB Stuttgart II | - | SV Wehen Wiesbaden | 3:0 | ||||
| 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 | ||||
| 12. Round | 02/10/2009 | Holstein Kiel | - | VfB Stuttgart II | 2:0 | ||||
| 13. Round | 18/10/2009 | VfB Stuttgart II | - | Wacker Burghausen | 1:0 | ||||
| 14. Round | 24/10/2009 | Eintracht Braunschweig | - | VfB Stuttgart II | 4:3 | ||||
| 15. Round | 30/10/2009 | VfB Stuttgart II | - | Werder Bremen II | 0:1 | ||||
| 21. Round | 19/12/2009 | 1. FC Heidenheim 1846 | - | VfB Stuttgart II | 2:1 | ||||
| 37. Round | 30/04/2010 | VfB Stuttgart II | - | SpVgg Unterhaching | 3:1 | ||||
| 38. Round | 08/05/2010 | FC Carl Zeiss Jena | - | VfB Stuttgart II | 1:2 |  |
Germany