| 6. Round | 24/09/1999 | Bayern München | - | VfB Stuttgart | 0:1 | ||||
| 9. Round | 23/10/1999 | Hertha BSC | - | VfB Stuttgart | 1:1 | ||||
| 11. Round | 06/11/1999 | VfL Wolfsburg | - | VfB Stuttgart | 0:2 |  |
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| 12. Round | 20/11/1999 | VfB Stuttgart | - | SSV Ulm 1846 | 2:0 | ||||
| 13. Round | 26/11/1999 | SC Freiburg | - | VfB Stuttgart | 0:2 | ||||
| 14. Round | 04/12/1999 | VfB Stuttgart | - | TSV 1860 München | 1:3 | ||||
| 15. Round | 11/12/1999 | Borussia Dortmund | - | VfB Stuttgart | 1:1 | ||||
| 17. Round | 17/12/1999 | Arminia Bielefeld | - | VfB Stuttgart | 1:2 | ||||
| 21. Round | 19/02/2000 | VfB Stuttgart | - | SpVgg Unterhaching | 0:2 | ||||
| 25. Round | 18/03/2000 | FC Schalke 04 | - | VfB Stuttgart | 3:0 | ||||
| 27. Round | 02/04/2000 | 1. FC Kaiserslautern | - | VfB Stuttgart | 1:2 | ||||
| 28. Round | 08/04/2000 | VfB Stuttgart | - | VfL Wolfsburg | 2:5 | ||||
| 29. Round | 11/04/2000 | SSV Ulm 1846 | - | VfB Stuttgart | 1:1 | ||||
| 31. Round | 22/04/2000 | TSV 1860 München | - | VfB Stuttgart | 1:1 | |
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| 32. Round | 29/04/2000 | VfB Stuttgart | - | Borussia Dortmund | 1:2 | ||||
| 34. Round | 20/05/2000 | VfB Stuttgart | - | Arminia Bielefeld | 3:3 |
Egypt