| 3. Round | 17/08/2008 | Kickers Offenbach [Youth] | - | Jahn Regensburg [Youth] | 1:4 | ||||
| 2. Round | 23/08/2008 | Karlsruher SC [Youth] | - | Kickers Offenbach [Youth] | 3:2 | ||||
| 5. Round | 28/09/2008 | Kickers Offenbach [Youth] | - | TSV 1860 München [Youth] | 1:1 | ||||
| 7. Round | 12/11/2008 | Eintracht Frankfurt [Youth] | - | Kickers Offenbach [Youth] | 3:1 | ||||
| 10. Round | 16/11/2008 | Kickers Offenbach [Youth] | - | SpVgg Unterhaching [Youth] | 3:2 | ||||
| 11. Round | 30/11/2008 | Bayern München [Youth] | - | Kickers Offenbach [Youth] | 2:2 | ||||
| 12. Round | 06/12/2008 | Kickers Offenbach [Youth] | - | VfB Stuttgart [Youth] | 2:2 | ||||
| 13. Round | 13/12/2008 | SC Freiburg [Youth] | - | Kickers Offenbach [Youth] | 3:1 | ||||
| 17. Round | 08/03/2009 | Kickers Offenbach [Youth] | - | 1899 Hoffenheim [Youth] | 0:0 | ||||
| 18. Round | 15/03/2009 | TSV 1860 München [Youth] | - | Kickers Offenbach [Youth] | 0:2 | ||||
| 19. Round | 22/03/2009 | Kickers Offenbach [Youth] | - | 1. FSV Mainz 05 [Youth] | 1:1 | ||||
| 25. Round | 07/06/2009 | VfB Stuttgart [Youth] | - | Kickers Offenbach [Youth] | 5:2 | ||||
| 26. Round | 14/06/2009 | Kickers Offenbach [Youth] | - | SC Freiburg [Youth] | 0:4 |
Germany