| 3. Round | 17/08/2008 | Bayern München [Youth] | - | VfB Stuttgart [Youth] | 2:1 |  |
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| 9. Round | 20/09/2008 | VfB Stuttgart [Youth] | - | 1899 Hoffenheim [Youth] | 2:1 | ||||
| 5. Round | 27/09/2008 | VfB Stuttgart [Youth] | - | SC Freiburg [Youth] | 0:0 | ||||
| 6. Round | 04/10/2008 | SpVgg Greuther Fürth [Youth] | - | VfB Stuttgart [Youth] | 2:0 | ||||
| 7. Round | 25/10/2008 | VfB Stuttgart [Youth] | - | Karlsruher SC [Youth] | 2:3 | ||||
| 8. Round | 02/11/2008 | Jahn Regensburg [Youth] | - | VfB Stuttgart [Youth] | 2:2 |  |
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| 10. Round | 16/11/2008 | TSV 1860 München [Youth] | - | VfB Stuttgart [Youth] | 0:0 | ||||
| 11. Round | 29/11/2008 | VfB Stuttgart [Youth] | - | 1. FSV Mainz 05 [Youth] | 3:2 | ||||
| 12. Round | 06/12/2008 | Kickers Offenbach [Youth] | - | VfB Stuttgart [Youth] | 2:2 | ||||
| 25. Round | 07/06/2009 | VfB Stuttgart [Youth] | - | Kickers Offenbach [Youth] | 5:2 | |
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| 26. Round | 14/06/2009 | FC 08 Villingen [Youth] | - | VfB Stuttgart [Youth] | 0:8 | |
Germany