| 10. Round | 16/11/2008 | Wuppertaler SV [Youth] | - | 1. FC Köln [Youth] | 0:3 | ||||
| 11. Round | 30/11/2008 | SV Bergisch Gladbach 09 [Youth] | - | Wuppertaler SV [Youth] | 1:2 | ||||
| 12. Round | 07/12/2008 | Wuppertaler SV [Youth] | - | Borussia Dortmund [Youth] | 1:6 |  |
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| 13. Round | 14/12/2008 | Alemannia Aachen [Youth] | - | Wuppertaler SV [Youth] | 1:0 | ||||
| 14. Round | 15/02/2009 | VfL Bochum [Youth] | - | Wuppertaler SV [Youth] | 6:2 | ||||
| 15. Round | 22/02/2009 | Wuppertaler SV [Youth] | - | Arminia Bielefeld [Youth] | 1:1 | ||||
| 16. Round | 01/03/2009 | Wuppertaler SV [Youth] | - | FC Schalke 04 [Youth] | 0:3 | ||||
| 17. Round | 08/03/2009 | Bayer Leverkusen [Youth] | - | Wuppertaler SV [Youth] | 4:2 | ||||
| 19. Round | 22/03/2009 | Bor. Mönchengladbach [Youth] | - | Wuppertaler SV [Youth] | 4:1 | ||||
| 20. Round | 05/04/2009 | Wuppertaler SV [Youth] | - | Rot-Weiss Essen [Youth] | 2:1 | ||||
| 26. Round | 14/06/2009 | Wuppertaler SV [Youth] | - | Alemannia Aachen [Youth] | 2:1 |
Germany