| 1. Round | 29/07/1989 | VfB Stuttgart | - | Karlsruher SC | 2:0 | ||||
| 18. Round | 25/11/1989 | Karlsruher SC | - | VfB Stuttgart | 1:0 | ||||
| 19. Round | 02/12/1989 | VfB Stuttgart | - | 1. FC Köln | 3:1 | ||||
| 20. Round | 09/12/1989 | Waldhof Mannheim | - | VfB Stuttgart | 2:1 |  |
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| 24. Round | 10/03/1990 | VfB Stuttgart | - | Fortuna Düsseldorf | 4:0 | ||||
| 25. Round | 17/03/1990 | Bayer 05 Uerdingen | - | VfB Stuttgart | 4:1 | ||||
| 26. Round | 24/03/1990 | VfB Stuttgart | - | 1. FC Kaiserslautern | 0:1 | ||||
| 27. Round | 31/03/1990 | Bayern München | - | VfB Stuttgart | 3:1 | ||||
| 30. Round | 21/04/1990 | VfB Stuttgart | - | Werder Bremen | 3:1 |  |
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| 31. Round | 28/04/1990 | Borussia Dortmund | - | VfB Stuttgart | 2:0 | ||||
| 32. Round | 01/05/1990 | VfB Stuttgart | - | 1. FC Nürnberg | 4:0 | ||||
| 33. Round | 05/05/1990 | Bor. Mönchengladbach | - | VfB Stuttgart | 3:1 | ||||
| 34. Round | 12/05/1990 | VfB Stuttgart | - | FC 08 Homburg | 2:2 |
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