| 3. Round | 30/08/2008 | VfB Stuttgart [Youth B] | - | 1. FC Nürnberg [Youth B] | 1:1 | ||||
| 8. Round | 01/11/2008 | VfB Stuttgart [Youth B] | - | Karlsruher SC [Youth B] | 5:0 | ||||
| 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 | ||||
| 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 | ||||
| 25. Round | 07/06/2009 | Kickers Offenbach [Youth B] | - | VfB Stuttgart [Youth B] | 1:2 |
Germany
Poland