| 6. Round | 04/10/2008 | 1. FSV Mainz 05 [Youth] | - | Kickers Offenbach [Youth] | 1:0 | ||||
| 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 | ||||
| 14. Round | 14/02/2009 | SpVgg Greuther Fürth [Youth] | - | Kickers Offenbach [Youth] | 6:0 | ||||
| 16. Round | 01/03/2009 | Jahn Regensburg [Youth] | - | Kickers Offenbach [Youth] | 2:0 | ||||
| 19. Round | 22/03/2009 | Kickers Offenbach [Youth] | - | 1. FSV Mainz 05 [Youth] | 1:1 | ||||
| 15. Round | 09/04/2009 | Kickers Offenbach [Youth] | - | Karlsruher SC [Youth] | 4:2 | ||||
| 21. Round | 19/04/2009 | FC 08 Villingen [Youth] | - | Kickers Offenbach [Youth] | 1:3 |  |
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| 22. Round | 26/04/2009 | Kickers Offenbach [Youth] | - | 1. FC Kaiserslautern [Youth] | 2:1 | |
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| 20. Round | 01/05/2009 | Kickers Offenbach [Youth] | - | Eintracht Frankfurt [Youth] | 1:3 | ||||
| 24. Round | 10/05/2009 | Kickers Offenbach [Youth] | - | Bayern München [Youth] | 0:0 | ||||
| 23. Round | 17/05/2009 | SpVgg Unterhaching [Youth] | - | Kickers Offenbach [Youth] | 3:2 |
Germany