| 1. Round | 14/08/1998 | VfB Stuttgart | - | Borussia Dortmund | 2:1 | ||||
| 4. Round | 11/09/1998 | Eintracht Frankfurt | - | VfB Stuttgart | 1:1 |  |
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| 5. Round | 19/09/1998 | VfB Stuttgart | - | TSV 1860 München | 0:1 | ||||
| 10. Round | 31/10/1998 | VfB Stuttgart | - | VfL Bochum | 4:2 | ||||
| 11. Round | 08/11/1998 | Bayer Leverkusen | - | VfB Stuttgart | 0:0 | ||||
| 24. Round | 03/04/1999 | VfB Stuttgart | - | MSV Duisburg | 0:0 | ||||
| 25. Round | 10/04/1999 | Hertha BSC | - | VfB Stuttgart | 2:0 | ||||
| 26. Round | 13/04/1999 | VfB Stuttgart | - | 1. FC Nürnberg | 0:0 | |
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| 27. Round | 17/04/1999 | VfL Bochum | - | VfB Stuttgart | 3:3 | ||||
| 28. Round | 23/04/1999 | VfB Stuttgart | - | Bayer Leverkusen | 0:1 | ||||
| 32. Round | 15/05/1999 | VfB Stuttgart | - | SC Freiburg | 3:1 | |
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| 33. Round | 22/05/1999 | Hamburger SV | - | VfB Stuttgart | 3:1 |  |
Germany