| 12. Round | 23/11/1958 | Rot-Weiss Essen | - | 1. FC Köln | 2:4 |  |
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| 13. Round | 30/11/1958 | Rot-Weiss Essen | - | Rot-Weiß Oberhausen | 1:0 | |
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| 14. Round | 07/12/1958 | Alemannia Aachen | - | Rot-Weiss Essen | 0:2 | ||||
| 15. Round | 14/12/1958 | SV Sodingen | - | Rot-Weiss Essen | 0:1 | ||||
| 16. Round | 04/01/1959 | Borussia Dortmund | - | Rot-Weiss Essen | 4:2 | ||||
| 18. Round | 18/01/1959 | STV Horst-Emscher | - | Rot-Weiss Essen | 1:4 | ||||
| 19. Round | 25/01/1959 | Rot-Weiss Essen | - | Duisburger SpV | 2:0 | ||||
| 20. Round | 01/02/1959 | Borussia VfL M.-Gladbach | - | Rot-Weiss Essen | 0:6 | |
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| 21. Round | 08/02/1959 | Rot-Weiss Essen | - | Westfalia Herne | 2:2 | ||||
| 22. Round | 15/02/1959 | VfL Bochum | - | Rot-Weiss Essen | 1:2 | ||||
| 23. Round | 22/02/1959 | Preußen Münster | - | Rot-Weiss Essen | 1:2 | ||||
| 24. Round | 28/02/1959 | Rot-Weiss Essen | - | FC Schalke 04 | 1:0 | ||||
| 25. Round | 08/03/1959 | Meidericher SV | - | Rot-Weiss Essen | 2:1 | ||||
| 28. Round | 05/04/1959 | Rot-Weiß Oberhausen | - | Rot-Weiss Essen | 1:1 | ||||
| 17. Round | 12/04/1959 | Rot-Weiss Essen | - | SC Viktoria 04 Köln | 2:2 |
Germany