| 6. Round | 29/10/2008 | VfB Stuttgart [Youth B] | - | SC Freiburg [Youth B] | 8:0 | ||||
| 9. Round | 08/11/2008 | 1899 Hoffenheim [Youth B] | - | VfB Stuttgart [Youth B] | 0:2 | ||||
| 10. Round | 15/11/2008 | VfB Stuttgart [Youth B] | - | TSV 1860 München [Youth B] | 1:2 |  |
|||
| 15. Round | 21/02/2009 | VfB Stuttgart [Youth B] | - | Eintracht Frankfurt [Youth B] | 1:1 | ||||
| 16. Round | 01/03/2009 | 1. FC Nürnberg [Youth B] | - | VfB Stuttgart [Youth B] | 1:2 | |
|||
| 17. Round | 07/03/2009 | VfB Stuttgart [Youth B] | - | Bayern München [Youth B] | 1:2 | ||||
| 18. Round | 14/03/2009 | VfB Stuttgart [Youth B] | - | SSV Ulm 1846 [Youth B] | 1:0 | |
|||
| 19. Round | 21/03/2009 | SC Freiburg [Youth B] | - | VfB Stuttgart [Youth B] | 1:2 | ||||
| 20. Round | 04/04/2009 | VfB Stuttgart [Youth B] | - | SpVgg Greuther Fürth [Youth B] | 3:0 | ||||
| 22. Round | 25/04/2009 | VfB Stuttgart [Youth B] | - | 1899 Hoffenheim [Youth B] | 0:2 | ||||
| 23. Round | 21/05/2009 | TSV 1860 München [Youth B] | - | VfB Stuttgart [Youth B] | 2:1 | |
|||
| 24. Round | 24/05/2009 | VfB Stuttgart [Youth B] | - | 1. FSV Mainz 05 [Youth B] | 5:2 | |
Germany