| 1. Round | 17/08/1958 | TSV 1860 München | - | 1. FC Schweinfurt 05 | 3:3 |  |
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| 2. Round | 24/08/1958 | TSG Ulm 1846 | - | TSV 1860 München | 2:2 | |
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| 3. Round | 31/08/1958 | TSV 1860 München | - | Waldhof Mannheim | 4:3 | ||||
| 4. Round | 07/09/1958 | Frankfurter SG Eintracht | - | TSV 1860 München | 3:0 | ||||
| 5. Round | 14/09/1958 | VfB Stuttgart | - | TSV 1860 München | 0:2 | ||||
| 6. Round | 20/09/1958 | TSV 1860 München | - | Bayern München | 1:2 | ||||
| 8. Round | 12/10/1958 | TSV 1860 München | - | FSV Frankfurt | 2:2 | |
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| 9. Round | 19/10/1958 | Karlsruher SC | - | TSV 1860 München | 1:1 | ||||
| 10. Round | 02/11/1958 | TSV 1860 München | - | BC Augsburg | 7:1 | |
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| 12. Round | 23/11/1958 | TSV 1860 München | - | 1. FC Nürnberg | 2:1 | ||||
| 15. Round | 14/12/1958 | SpVgg Fürth | - | TSV 1860 München | 1:2 | ||||
| 16. Round | 11/01/1959 | 1. FC Schweinfurt 05 | - | TSV 1860 München | 1:2 | |
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| 17. Round | 18/01/1959 | TSV 1860 München | - | TSG Ulm 1846 | 0:2 | ||||
| 25. Round | 22/03/1959 | BC Augsburg | - | TSV 1860 München | 2:0 | ||||
| 29. Round | 03/05/1959 | Kickers Offenbach | - | TSV 1860 München | 2:3 | |
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| 30. Round | 10/05/1959 | TSV 1860 München | - | SpVgg Fürth | 1:1 | |
Germany