| 1. Round | 14/08/1999 | VfB Stuttgart | - | Werder Bremen | 0:0 | ||||
| 2. Round | 21/08/1999 | Hamburger SV | - | VfB Stuttgart | 3:0 | ||||
| 3. Round | 28/08/1999 | VfB Stuttgart | - | Bayer Leverkusen | 1:2 | ||||
| 6. Round | 24/09/1999 | Bayern München | - | VfB Stuttgart | 0:1 |  |
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| 7. Round | 01/10/1999 | Eintracht Frankfurt | - | VfB Stuttgart | 0:1 | ||||
| 10. Round | 31/10/1999 | VfB Stuttgart | - | 1. FC Kaiserslautern | 0:1 |
Germany