| 2. Round | 24/08/2008 | 1. FSV Mainz 05 [Youth B] | - | 1899 Hoffenheim [Youth B] | 1:3 | ||||
| 3. Round | 31/08/2008 | 1899 Hoffenheim [Youth B] | - | Kickers Offenbach [Youth B] | 4:2 |  |
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| 1. Round | 03/09/2008 | 1899 Hoffenheim [Youth B] | - | TSV 1860 München [Youth B] | 1:3 | ||||
| 21. Round | 06/09/2008 | 1899 Hoffenheim [Youth B] | - | Bayern München [Youth B] | 0:0 | ||||
| 11. Round | 29/11/2008 | 1899 Hoffenheim [Youth B] | - | SpVgg Greuther Fürth [Youth B] | 0:4 | ||||
| 12. Round | 07/12/2008 | Karlsruher SC [Youth B] | - | 1899 Hoffenheim [Youth B] | 4:2 | ||||
| 13. Round | 13/12/2008 | 1899 Hoffenheim [Youth B] | - | SSV Ulm 1846 [Youth B] | 1:1 | ||||
| 15. Round | 21/02/2009 | 1899 Hoffenheim [Youth B] | - | 1. FSV Mainz 05 [Youth B] | 0:3 |
Germany