| 10. Round | 16/11/2008 | Rot-Weiss Essen [Youth B] | - | Bor. Mönchengladbach [Youth B] | 0:5 | ||||
| 11. Round | 15/02/2009 | SF Troisdorf 05 [Youth B] | - | Rot-Weiss Essen [Youth B] | 2:1 | ||||
| 16. Round | 01/03/2009 | Rot-Weiss Essen [Youth B] | - | FC Schalke 04 [Youth B] | 3:3 |  |
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| 17. Round | 08/03/2009 | Borussia Dortmund [Youth B] | - | Rot-Weiss Essen [Youth B] | 3:0 | ||||
| 18. Round | 15/03/2009 | Rot-Weiss Essen [Youth B] | - | Alemannia Aachen [Youth B] | 2:1 | ||||
| 19. Round | 22/03/2009 | Arminia Bielefeld [Youth B] | - | Rot-Weiss Essen [Youth B] | 2:2 | ||||
| 15. Round | 25/03/2009 | 1. FC Köln [Youth B] | - | Rot-Weiss Essen [Youth B] | 3:0 | ||||
| 20. Round | 05/04/2009 | Rot-Weiss Essen [Youth B] | - | Wuppertaler SV [Youth B] | 0:0 | ||||
| 24. Round | 24/05/2009 | Rot-Weiss Essen [Youth B] | - | SF Troisdorf 05 [Youth B] | 2:3 | ||||
| 23. Round | 28/05/2009 | Bor. Mönchengladbach [Youth B] | - | Rot-Weiss Essen [Youth B] | 3:0 | ||||
| 25. Round | 07/06/2009 | Rot-Weiss Essen [Youth B] | - | VfL Bochum [Youth B] | 1:2 | ||||
| 26. Round | 14/06/2009 | Preußen Münster [Youth B] | - | Rot-Weiss Essen [Youth B] | 4:1 | |
Germany