| 1. Round | 17/08/2008 | SpVgg Greuther Fürth [Youth B] | - | Kickers Offenbach [Youth B] | 5:1 | ||||
| 21. Round | 06/09/2008 | Kickers Offenbach [Youth B] | - | 1. FC Kaiserslautern [Youth B] | 0:4 | ||||
| 14. Round | 11/10/2008 | Kickers Offenbach [Youth B] | - | SpVgg Greuther Fürth [Youth B] | 5:4 |  |
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| 7. Round | 26/10/2008 | Kickers Offenbach [Youth B] | - | 1. FC Saarbrücken [Youth B] | 1:2 |  |
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| 8. Round | 01/11/2008 | 1. FC Kaiserslautern [Youth B] | - | Kickers Offenbach [Youth B] | 3:0 | |
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| 9. Round | 09/11/2008 | Kickers Offenbach [Youth B] | - | Eintracht Frankfurt [Youth B] | 1:1 | |
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| 10. Round | 16/11/2008 | 1. FC Nürnberg [Youth B] | - | Kickers Offenbach [Youth B] | 2:1 | ||||
| 11. Round | 30/11/2008 | Kickers Offenbach [Youth B] | - | Bayern München [Youth B] | 2:3 | |
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| 12. Round | 06/12/2008 | VfB Stuttgart [Youth B] | - | Kickers Offenbach [Youth B] | 4:0 | ||||
| 13. Round | 14/12/2008 | Kickers Offenbach [Youth B] | - | SC Freiburg [Youth B] | 0:2 | ||||
| 15. Round | 22/02/2009 | Karlsruher SC [Youth B] | - | Kickers Offenbach [Youth B] | 5:0 | ||||
| 18. Round | 15/03/2009 | Kickers Offenbach [Youth B] | - | 1. FSV Mainz 05 [Youth B] | 1:2 |
Germany