| 3. Round | 17/08/2008 | Bayern München [Youth] | - | VfB Stuttgart [Youth] | 2:1 | ||||
| 2. Round | 23/08/2008 | VfB Stuttgart [Youth] | - | SpVgg Unterhaching [Youth] | 0:3 | ||||
| 1. Round | 30/08/2008 | 1. FC Kaiserslautern [Youth] | - | VfB Stuttgart [Youth] | 0:3 | ||||
| 4. Round | 13/09/2008 | VfB Stuttgart [Youth] | - | Eintracht Frankfurt [Youth] | 3:1 | ||||
| 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 | ||||
| 25. Round | 07/06/2009 | VfB Stuttgart [Youth] | - | Kickers Offenbach [Youth] | 5:2 | ||||
| 26. Round | 14/06/2009 | FC 08 Villingen [Youth] | - | VfB Stuttgart [Youth] | 0:8 |
Germany