| 1. Round | 13/08/1999 | VfL Wolfsburg | - | TSV 1860 München | 2:1 | ||||
| 2. Round | 21/08/1999 | Borussia Dortmund | - | VfL Wolfsburg | 2:1 |  |
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| 3. Round | 28/08/1999 | VfL Wolfsburg | - | Hansa Rostock | 2:0 | |
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| 4. Round | 10/09/1999 | Arminia Bielefeld | - | VfL Wolfsburg | 0:0 | |
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| 5. Round | 19/09/1999 | VfL Wolfsburg | - | Werder Bremen | 2:7 | ||||
| 7. Round | 02/10/1999 | VfL Wolfsburg | - | Bayer Leverkusen | 3:1 | ||||
| 8. Round | 17/10/1999 | SpVgg Unterhaching | - | VfL Wolfsburg | 1:1 | ||||
| 10. Round | 30/10/1999 | Bayern München | - | VfL Wolfsburg | 5:0 | ||||
| 11. Round | 06/11/1999 | VfL Wolfsburg | - | VfB Stuttgart | 0:2 | |
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| 14. Round | 05/12/1999 | 1. FC Kaiserslautern | - | VfL Wolfsburg | 2:2 | ||||
| 15. Round | 12/12/1999 | VfL Wolfsburg | - | Eintracht Frankfurt | 1:0 | ||||
| 16. Round | 15/12/1999 | VfL Wolfsburg | - | SSV Ulm 1846 | 1:2 | ||||
| 17. Round | 18/12/1999 | SC Freiburg | - | VfL Wolfsburg | 1:1 | ||||
| 20. Round | 12/02/2000 | Hansa Rostock | - | VfL Wolfsburg | 1:1 |
Germany