| 16. Round | 28/02/2009 | VfB Stuttgart [Youth] | - | Bayern München [Youth] | 3:1 | ||||
| 13. Round | 11/03/2009 | VfB Stuttgart [Youth] | - | FC 08 Villingen [Youth] | 5:1 |  |
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| 18. Round | 14/03/2009 | SC Freiburg [Youth] | - | VfB Stuttgart [Youth] | 4:0 | ||||
| 19. Round | 21/03/2009 | VfB Stuttgart [Youth] | - | SpVgg Greuther Fürth [Youth] | 2:1 | ||||
| 14. Round | 29/03/2009 | VfB Stuttgart [Youth] | - | 1. FC Kaiserslautern [Youth] | 1:1 | |
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| 20. Round | 04/04/2009 | Karlsruher SC [Youth] | - | VfB Stuttgart [Youth] | 1:0 | ||||
| 21. Round | 18/04/2009 | VfB Stuttgart [Youth] | - | Jahn Regensburg [Youth] | 3:1 | |
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| 22. Round | 26/04/2009 | 1899 Hoffenheim [Youth] | - | VfB Stuttgart [Youth] | 3:3 | |
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| 15. Round | 01/05/2009 | SpVgg Unterhaching [Youth] | - | VfB Stuttgart [Youth] | 4:2 | ||||
| 24. Round | 10/05/2009 | 1. FSV Mainz 05 [Youth] | - | VfB Stuttgart [Youth] | 0:1 | ||||
| 23. Round | 16/05/2009 | VfB Stuttgart [Youth] | - | TSV 1860 München [Youth] | 0:1 |
Germany