| 6. Round | 05/10/2008 | Kickers Offenbach [Youth B] | - | SSV Ulm 1846 [Youth B] | 1:1 | ||||
| 14. Round | 11/10/2008 | Kickers Offenbach [Youth B] | - | SpVgg Greuther Fürth [Youth B] | 5:4 | ||||
| 7. Round | 26/10/2008 | Kickers Offenbach [Youth B] | - | 1. FC Saarbrücken [Youth B] | 1:2 | ||||
| 8. Round | 01/11/2008 | 1. FC Kaiserslautern [Youth B] | - | Kickers Offenbach [Youth B] | 3:0 | ||||
| 9. Round | 09/11/2008 | Kickers Offenbach [Youth B] | - | Eintracht Frankfurt [Youth B] | 1:1 | ||||
| 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 | ||||
| 15. Round | 22/02/2009 | Karlsruher SC [Youth B] | - | Kickers Offenbach [Youth B] | 5:0 | ||||
| 17. Round | 07/03/2009 | TSV 1860 München [Youth B] | - | Kickers Offenbach [Youth B] | 1:0 | ||||
| 18. Round | 15/03/2009 | Kickers Offenbach [Youth B] | - | 1. FSV Mainz 05 [Youth B] | 1:2 | ||||
| 19. Round | 22/03/2009 | SSV Ulm 1846 [Youth B] | - | Kickers Offenbach [Youth B] | 2:1 |
Germany