| 1. Round | 15/08/2009 | VfB Stuttgart [Youth] | - | Waldhof Mannheim [Youth] | 4:0 |  |
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| 2. Round | 22/08/2009 | 1. FC Kaiserslautern [Youth] | - | VfB Stuttgart [Youth] | 1:4 | |
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| 3. Round | 29/08/2009 | VfB Stuttgart [Youth] | - | Eintracht Frankfurt [Youth] | 5:1 | |
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| 4. Round | 12/09/2009 | TSV 1860 München [Youth] | - | VfB Stuttgart [Youth] | 0:1 | ||||
| 5. Round | 27/09/2009 | VfB Stuttgart [Youth] | - | 1. FSV Mainz 05 [Youth] | 3:2 | ||||
| 6. Round | 03/10/2009 | SpVgg Greuther Fürth [Youth] | - | VfB Stuttgart [Youth] | 0:2 | ||||
| 7. Round | 18/10/2009 | VfB Stuttgart [Youth] | - | SC Freiburg [Youth] | 0:3 | ||||
| 8. Round | 01/11/2009 | 1. FC Nürnberg [Youth] | - | VfB Stuttgart [Youth] | 0:2 | ||||
| 9. Round | 08/11/2009 | Bayern München [Youth] | - | VfB Stuttgart [Youth] | 1:2 | ||||
| 10. Round | 14/11/2009 | VfB Stuttgart [Youth] | - | SV Darmstadt 98 [Youth] | 4:1 | ||||
| 11. Round | 22/11/2009 | Jahn Regensburg [Youth] | - | VfB Stuttgart [Youth] | 0:4 | ||||
| 12. Round | 28/11/2009 | VfB Stuttgart [Youth] | - | 1899 Hoffenheim [Youth] | 3:1 | |
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| 13. Round | 05/12/2009 | Karlsruher SC [Youth] | - | VfB Stuttgart [Youth] | 1:1 |
Germany