| 1. Round | 29/07/1989 | Hessen Kassel | - | Blau-Weiß 90 Berlin | 1:1 | ||||
| 2. Round | 06/08/1989 | Preußen Münster | - | Hessen Kassel | 1:1 |  |
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| 3. Round | 12/08/1989 | Hessen Kassel | - | SC Freiburg | 2:5 | ||||
| 4. Round | 16/08/1989 | SV Darmstadt 98 | - | Hessen Kassel | 0:1 | ||||
| 5. Round | 23/08/1989 | Hessen Kassel | - | VfL Osnabrück | 1:5 | ||||
| 6. Round | 27/08/1989 | SpVgg Bayreuth | - | Hessen Kassel | 5:1 | |
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| 7. Round | 02/09/1989 | Hessen Kassel | - | Rot-Weiss Essen | 0:1 |  |
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| 14. Round | 22/10/1989 | FC Schalke 04 | - | Hessen Kassel | 2:0 | ||||
| 15. Round | 28/10/1989 | Hessen Kassel | - | SG Wattenscheid 09 | 0:3 | ||||
| 16. Round | 04/11/1989 | SV Meppen | - | Hessen Kassel | 0:1 | ||||
| 17. Round | 11/11/1989 | Fortuna Köln | - | Hessen Kassel | 0:1 | ||||
| 18. Round | 22/11/1989 | Hessen Kassel | - | SpVgg Unterhaching | 3:2 | ||||
| 21. Round | 02/12/1989 | Hessen Kassel | - | Preußen Münster | 0:0 | ||||
| 23. Round | 16/12/1989 | Hessen Kassel | - | SV Darmstadt 98 | 0:0 |
Germany