| 2. Round | 02/08/2008 | 1. FC Union Berlin | - | VfB Stuttgart II | 3:1 | ||||
| 3. Round | 16/08/2008 | VfB Stuttgart II | - | Wuppertaler SV | 2:0 |  |
|||
| 4. Round | 23/08/2008 | Dynamo Dresden | - | VfB Stuttgart II | 1:0 | ||||
| 5. Round | 30/08/2008 | VfB Stuttgart II | - | Eintracht Braunschweig | 4:0 | |
|||
| 12. Round | 29/10/2008 | SpVgg Unterhaching | - | VfB Stuttgart II | 0:2 | |
|||
| 13. Round | 02/11/2008 | VfB Stuttgart II | - | SV Sandhausen | 1:1 | |
|||
| 14. Round | 08/11/2008 | Jahn Regensburg | - | VfB Stuttgart II | 1:1 | |
|||
| 15. Round | 16/11/2008 | VfB Stuttgart II | - | Erzgebirge Aue | 3:0 | ||||
| 16. Round | 21/11/2008 | Rot-Weiß Erfurt | - | VfB Stuttgart II | 1:0 |  |
|||
| 24. Round | 27/02/2009 | Eintracht Braunschweig | - | VfB Stuttgart II | 2:0 | ||||
| 27. Round | 20/03/2009 | VfB Stuttgart II | - | Werder Bremen II | 2:0 | |
|||
| 31. Round | 11/04/2009 | VfB Stuttgart II | - | SpVgg Unterhaching | 1:3 | |
|||
| 32. Round | 17/04/2009 | SV Sandhausen | - | VfB Stuttgart II | 1:1 | ||||
| 33. Round | 24/04/2009 | VfB Stuttgart II | - | Jahn Regensburg | 1:2 | ||||
| 34. Round | 02/05/2009 | Erzgebirge Aue | - | VfB Stuttgart II | 0:3 | |
|
||
| 35. Round | 10/05/2009 | VfB Stuttgart II | - | Rot-Weiß Erfurt | 3:1 |
Germany
