| 1. Round | 15/08/2008 | Sportfreunde Lotte | - | Rot-Weiss Essen | 1:4 | ||||
| 2. Round | 22/08/2008 | Rot-Weiss Essen | - | FC Schalke 04 II | 4:0 | ||||
| 4. Round | 14/09/2008 | Rot-Weiss Essen | - | VfL Bochum II | 1:1 | ||||
| 7. Round | 03/10/2008 | BV Cloppenburg | - | Rot-Weiss Essen | 0:0 | ||||
| 9. Round | 26/10/2008 | Preußen Münster | - | Rot-Weiss Essen | 3:1 | ||||
| 10. Round | 29/10/2008 | Rot-Weiss Essen | - | SC Verl | 2:1 | ||||
| 11. Round | 01/11/2008 | Rot-Weiss Essen | - | 1. FSV Mainz 05 II | 5:0 |  |
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| 12. Round | 08/11/2008 | 1. FC Kleve | - | Rot-Weiss Essen | 2:2 | ||||
| 13. Round | 14/11/2008 | Rot-Weiss Essen | - | Bor. Mönchengladbach II | 3:1 |  |
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| 15. Round | 28/11/2008 | Rot-Weiss Essen | - | SV 07 Elversberg | 2:0 | |
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| 14. Round | 02/12/2008 | Bayer Leverkusen II | - | Rot-Weiss Essen | 4:2 | ||||
| 16. Round | 05/12/2008 | FSV Oggersheim | - | Rot-Weiss Essen | 1:1 | ||||
| 17. Round | 13/12/2008 | Rot-Weiss Essen | - | Borussia Dortmund II | 3:4 | ||||
| 18. Round | 19/12/2008 | Rot-Weiss Essen | - | Sportfreunde Lotte | 1:1 | ||||
| 23. Round | 20/03/2009 | Eintracht Trier | - | Rot-Weiss Essen | 1:1 |
Germany