| 13. Round | 30/11/1958 | 1. FC Phönix Lübeck | - | VfL Osnabrück | 0:4 |  |
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| 14. Round | 07/12/1958 | TuS Bremerhaven 93 | - | VfL Osnabrück | 1:5 | ||||
| 16. Round | 04/01/1959 | VfL Osnabrück | - | Altona 93 | 4:1 | ||||
| 17. Round | 11/01/1959 | VfV Hildesheim | - | VfL Osnabrück | 1:1 | ||||
| 19. Round | 25/01/1959 | Werder Bremen | - | VfL Osnabrück | 5:1 | ||||
| 20. Round | 01/02/1959 | VfL Osnabrück | - | Holstein Kiel | 1:0 | ||||
| 21. Round | 08/02/1959 | VfL Osnabrück | - | Concordia Hamburg | 1:0 | ||||
| 15. Round | 14/02/1959 | VfL Osnabrück | - | Hamburger SV | 1:1 | ||||
| 22. Round | 15/02/1959 | ASV Bergedorf | - | VfL Osnabrück | 2:0 | ||||
| 23. Round | 15/02/1959 | VfL Osnabrück | - | VfL Wolfsburg | 6:2 | |
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| 26. Round | 15/03/1959 | VfL Osnabrück | - | Eintracht Nordhorn | 5:0 | |
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| 27. Round | 22/03/1959 | VfR Neumünster | - | VfL Osnabrück | 0:0 | ||||
| 28. Round | 30/03/1959 | FC St. Pauli | - | VfL Osnabrück | 5:1 | ||||
| 18. Round | 12/04/1959 | VfL Osnabrück | - | Eintracht Braunschweig | 3:1 | ||||
| 29. Round | 19/04/1959 | VfL Osnabrück | - | TuS Bremerhaven 93 | 3:2 | ||||
| 30. Round | 26/04/1959 | VfL Osnabrück | - | 1. FC Phönix Lübeck | 2:1 | |
Germany