| 2. Round | 23/08/2008 | Bayer Leverkusen [Youth B] | - | Arminia Bielefeld [Youth B] | 0:1 | ||||
| 3. Round | 31/08/2008 | Arminia Bielefeld [Youth B] | - | MSV Duisburg [Youth B] | 2:0 |  |
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| 5. Round | 28/09/2008 | Arminia Bielefeld [Youth B] | - | SF Troisdorf 05 [Youth B] | 2:2 | ||||
| 14. Round | 12/10/2008 | Wuppertaler SV [Youth B] | - | Arminia Bielefeld [Youth B] | 2:3 | ||||
| 10. Round | 16/11/2008 | FC Schalke 04 [Youth B] | - | Arminia Bielefeld [Youth B] | 1:1 | ||||
| 11. Round | 30/11/2008 | Arminia Bielefeld [Youth B] | - | Borussia Dortmund [Youth B] | 0:0 | ||||
| 12. Round | 07/12/2008 | Alemannia Aachen [Youth B] | - | Arminia Bielefeld [Youth B] | 5:0 | ||||
| 13. Round | 14/12/2008 | Arminia Bielefeld [Youth B] | - | VfL Bochum [Youth B] | 1:1 | ||||
| 16. Round | 01/03/2009 | MSV Duisburg [Youth B] | - | Arminia Bielefeld [Youth B] | 1:1 | ||||
| 20. Round | 05/04/2009 | Preußen Münster [Youth B] | - | Arminia Bielefeld [Youth B] | 2:1 |
Germany