| 3. Round | 17/08/2008 | Kickers Offenbach [Youth] | - | Jahn Regensburg [Youth] | 1:4 | ||||
| 4. Round | 12/09/2008 | 1899 Hoffenheim [Youth] | - | Kickers Offenbach [Youth] | 0:0 | ||||
| 1. Round | 21/09/2008 | Kickers Offenbach [Youth] | - | SpVgg Greuther Fürth [Youth] | 3:1 | ||||
| 5. Round | 28/09/2008 | Kickers Offenbach [Youth] | - | TSV 1860 München [Youth] | 1:1 | ||||
| 6. Round | 04/10/2008 | 1. FSV Mainz 05 [Youth] | - | Kickers Offenbach [Youth] | 1:0 | ||||
| 8. Round | 02/11/2008 | Kickers Offenbach [Youth] | - | FC 08 Villingen [Youth] | 4:0 | ||||
| 9. Round | 08/11/2008 | 1. FC Kaiserslautern [Youth] | - | Kickers Offenbach [Youth] | 7:1 | ||||
| 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 | ||||
| 15. Round | 09/04/2009 | Kickers Offenbach [Youth] | - | Karlsruher SC [Youth] | 4:2 |
Germany