| 1. Round | 17/08/1958 | Rot-Weiss Essen | - | Borussia Dortmund | 1:2 |  |
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| 2. Round | 24/08/1958 | SC Viktoria 04 Köln | - | Rot-Weiss Essen | 1:3 | ||||
| 3. Round | 31/08/1958 | Rot-Weiss Essen | - | STV Horst-Emscher | 3:1 | |
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| 4. Round | 07/09/1958 | Duisburger SpV | - | Rot-Weiss Essen | 1:1 | ||||
| 5. Round | 14/09/1958 | Rot-Weiss Essen | - | Borussia VfL M.-Gladbach | 2:2 | ||||
| 6. Round | 28/09/1958 | Westfalia Herne | - | Rot-Weiss Essen | 2:0 | ||||
| 7. Round | 05/10/1958 | Rot-Weiss Essen | - | VfL Bochum | 2:3 | ||||
| 8. Round | 12/10/1958 | Rot-Weiss Essen | - | Preußen Münster | 0:1 | ||||
| 9. Round | 19/10/1958 | FC Schalke 04 | - | Rot-Weiss Essen | 2:2 | ||||
| 10. Round | 02/11/1958 | Rot-Weiss Essen | - | Meidericher SV | 0:1 | ||||
| 11. Round | 09/11/1958 | Fortuna Düsseldorf | - | Rot-Weiss Essen | 3:1 | ||||
| 16. Round | 04/01/1959 | Borussia Dortmund | - | Rot-Weiss Essen | 4:2 | ||||
| 26. Round | 15/03/1959 | Rot-Weiss Essen | - | Fortuna Düsseldorf | 1:0 | ||||
| 27. Round | 22/03/1959 | 1. FC Köln | - | Rot-Weiss Essen | 1:0 | ||||
| 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