| 3. Round | 29/08/1999 | SSV Ulm 1846 | - | Borussia Dortmund | 0:1 | ||||
| 4. Round | 10/09/1999 | Hansa Rostock | - | SSV Ulm 1846 | 2:1 |  |
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| 8. Round | 15/10/1999 | Bayer Leverkusen | - | SSV Ulm 1846 | 4:1 | ||||
| 14. Round | 04/12/1999 | Hertha BSC | - | SSV Ulm 1846 | 3:0 | ||||
| 28. Round | 08/04/2000 | Bayern München | - | SSV Ulm 1846 | 4:0 | ||||
| 29. Round | 11/04/2000 | SSV Ulm 1846 | - | VfB Stuttgart | 1:1 | ||||
| 30. Round | 14/04/2000 | FC Schalke 04 | - | SSV Ulm 1846 | 0:0 | ||||
| 31. Round | 22/04/2000 | SSV Ulm 1846 | - | Hertha BSC | 0:1 | ||||
| 32. Round | 29/04/2000 | 1. FC Kaiserslautern | - | SSV Ulm 1846 | 6:2 |
Trinidad & Tobago