| 4. Round | 16/08/1989 | SV Darmstadt 98 | - | Hessen Kassel | 0:1 | ||||
| 5. Round | 23/08/1989 | Hessen Kassel | - | VfL Osnabrück | 1:5 |  |
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| 6. Round | 27/08/1989 | SpVgg Bayreuth | - | Hessen Kassel | 5:1 | ||||
| 7. Round | 02/09/1989 | Hessen Kassel | - | Rot-Weiss Essen | 0:1 |  |
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| 8. Round | 09/09/1989 | Stuttgarter Kickers | - | Hessen Kassel | 2:0 | ||||
| 9. Round | 17/09/1989 | Hessen Kassel | - | Eintracht Braunschweig | 2:1 | ||||
| 10. Round | 20/09/1989 | MSV Duisburg | - | Hessen Kassel | 3:1 | ||||
| 11. Round | 30/09/1989 | Hessen Kassel | - | Alemannia Aachen | 1:5 | ||||
| 12. Round | 03/10/1989 | Hannover 96 | - | Hessen Kassel | 4:0 | ||||
| 13. Round | 14/10/1989 | Hessen Kassel | - | 1. FC Saarbrücken | 0:0 | ||||
| 14. Round | 22/10/1989 | FC Schalke 04 | - | Hessen Kassel | 2:0 | ||||
| 19. Round | 18/11/1989 | Hertha BSC | - | Hessen Kassel | 2:0 | |
Germany