| 1. Round | 16/08/1958 | FSV Frankfurt | - | Bayern München | 1:3 | ||||
| 2. Round | 24/08/1958 | Viktoria Aschaffenburg | - | FSV Frankfurt | 2:0 | ||||
| 3. Round | 31/08/1958 | FSV Frankfurt | - | 1. FC Nürnberg | 0:3 | ||||
| 4. Round | 07/09/1958 | SSV Reutlingen | - | FSV Frankfurt | 2:1 | ||||
| 5. Round | 13/09/1958 | FSV Frankfurt | - | 1. FC Schweinfurt 05 | 2:0 | ||||
| 7. Round | 05/10/1958 | FSV Frankfurt | - | VfB Stuttgart | 0:2 | ||||
| 8. Round | 12/10/1958 | TSV 1860 München | - | FSV Frankfurt | 2:2 |  |
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| 9. Round | 19/10/1958 | FSV Frankfurt | - | Kickers Offenbach | 0:2 | ||||
| 19. Round | 01/02/1959 | FSV Frankfurt | - | SSV Reutlingen | 5:1 | ||||
| 20. Round | 15/02/1959 | 1. FC Schweinfurt 05 | - | FSV Frankfurt | 3:0 | ||||
| 21. Round | 22/02/1959 | FSV Frankfurt | - | Frankfurter SG Eintracht | 1:2 | ||||
| 22. Round | 01/03/1959 | VfB Stuttgart | - | FSV Frankfurt | 6:1 | ||||
| 23. Round | 08/03/1959 | FSV Frankfurt | - | TSV 1860 München | 3:1 | ||||
| 24. Round | 15/03/1959 | Kickers Offenbach | - | FSV Frankfurt | 2:2 | ||||
| 25. Round | 22/03/1959 | FSV Frankfurt | - | SpVgg Fürth | 2:2 | ||||
| 28. Round | 25/04/1959 | FSV Frankfurt | - | Karlsruher SC | 4:3 |
Germany