| 16. Round | 29/03/2009 | Kickers Offenbach [Youth B] | - | 1899 Hoffenheim [Youth B] | 0:1 | ||||
| 20. Round | 05/04/2009 | 1. FC Saarbrücken [Youth B] | - | Kickers Offenbach [Youth B] | 0:2 | ||||
| 22. Round | 25/04/2009 | Eintracht Frankfurt [Youth B] | - | Kickers Offenbach [Youth B] | 2:3 | ||||
| 24. Round | 23/05/2009 | Bayern München [Youth B] | - | Kickers Offenbach [Youth B] | 2:1 | ||||
| 23. Round | 04/06/2009 | Kickers Offenbach [Youth B] | - | 1. FC Nürnberg [Youth B] | 3:4 | ||||
| 26. Round | 14/06/2009 | SC Freiburg [Youth B] | - | Kickers Offenbach [Youth B] | 6:3 |
Germany