| 7. Ronde | 25.10.2008 | FC Carl Zeiss Jena [A-jun] | - | 1. FC Union Berlin [A-jun] | 1:1 |  |
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| 8. Ronde | 01.11.2008 | Hansa Rostock [A-jun] | - | FC Carl Zeiss Jena [A-jun] | 1:0 | ||||
| 9. Ronde | 09.11.2008 | FC Carl Zeiss Jena [A-jun] | - | Hertha BSC [A-jun] | 1:2 | ||||
| 11. Ronde | 29.11.2008 | FC St. Pauli [A-jun] | - | FC Carl Zeiss Jena [A-jun] | 4:0 | ||||
| 13. Ronde | 14.12.2008 | Werder Bremen [A-jun] | - | FC Carl Zeiss Jena [A-jun] | 2:3 | ||||
| 21. Ronde | 18.04.2009 | FC Carl Zeiss Jena [A-jun] | - | Hansa Rostock [A-jun] | 1:1 | ||||
| 22. Ronde | 26.04.2009 | Hertha BSC [A-jun] | - | FC Carl Zeiss Jena [A-jun] | 1:3 | ||||
| 23. Ronde | 17.05.2009 | FC Carl Zeiss Jena [A-jun] | - | Hamburger SV [A-jun] | 2:2 | ||||
| 24. Ronde | 24.05.2009 | FC Carl Zeiss Jena [A-jun] | - | FC St. Pauli [A-jun] | 3:2 | |
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| 25. Ronde | 07.06.2009 | Rot-Weiß Erfurt [A-jun] | - | FC Carl Zeiss Jena [A-jun] | 3:0 | ||||
| 26. Ronde | 14.06.2009 | FC Carl Zeiss Jena [A-jun] | - | Werder Bremen [A-jun] | 1:2 |
Duitsland
Polen