| 1. Round | 28/07/2000 | TeBe Berlin | - | Rot-Weiss Essen | 2:0 | ||||
| 2. Round | 04/08/2000 | Rot-Weiss Essen | - | Sachsen Leipzig | 3:1 | ||||
| 3. Round | 12/08/2000 | Erzgebirge Aue | - | Rot-Weiss Essen | 1:0 |  |
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| 4. Round | 19/08/2000 | Rot-Weiss Essen | - | Fortuna Köln | 1:0 | ||||
| 5. Round | 23/08/2000 | SV Babelsberg 03 | - | Rot-Weiss Essen | 0:0 |  |
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| 8. Round | 16/09/2000 | Rot-Weiss Essen | - | Werder Bremen II | 3:1 | ||||
| 9. Round | 24/09/2000 | Borussia Dortmund II | - | Rot-Weiss Essen | 0:0 | ||||
| 10. Round | 29/09/2000 | Rot-Weiss Essen | - | SV Wilhelmshaven | 0:2 | ||||
| 11. Round | 07/10/2000 | Dresdner SC | - | Rot-Weiss Essen | 4:1 | ||||
| 13. Round | 20/10/2000 | Rot-Weiss Essen | - | SC Verl | 0:0 | ||||
| 14. Round | 27/10/2000 | KFC Uerdingen 05 | - | Rot-Weiss Essen | 0:2 | ||||
| 15. Round | 04/11/2000 | Rot-Weiss Essen | - | VfB Lübeck | 2:5 | ||||
| 16. Round | 11/11/2000 | Lüneburger SK | - | Rot-Weiss Essen | 3:1 |
Germany