| 8. Round | 16/10/1999 | Bayern München | - | Hertha BSC | 3:1 | ||||
| 12. Round | 20/11/1999 | Hertha BSC | - | 1. FC Kaiserslautern | 0:1 |  |
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| 14. Round | 04/12/1999 | Hertha BSC | - | SSV Ulm 1846 | 3:0 | |
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| 15. Round | 11/12/1999 | SC Freiburg | - | Hertha BSC | 0:1 | ||||
| 16. Round | 14/12/1999 | Hertha BSC | - | TSV 1860 München | 1:1 | ||||
| 23. Round | 04/03/2000 | Hertha BSC | - | SpVgg Unterhaching | 2:1 | |
Germany