| 1. Round | 15/08/1999 | Hertha BSC | - | Hansa Rostock | 5:2 |  |
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| 2. Round | 20/08/1999 | Arminia Bielefeld | - | Hertha BSC | 1:1 | ||||
| 3. Round | 28/08/1999 | Hertha BSC | - | Werder Bremen | 1:1 | ||||
| 4. Round | 11/09/1999 | Hamburger SV | - | Hertha BSC | 5:1 |  |
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| 5. Round | 18/09/1999 | Hertha BSC | - | Bayer Leverkusen | 0:0 | |
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| 6. Round | 25/09/1999 | SpVgg Unterhaching | - | Hertha BSC | 1:1 | ||||
| 7. Round | 02/10/1999 | Hertha BSC | - | MSV Duisburg | 2:1 | ||||
| 8. Round | 16/10/1999 | Bayern München | - | Hertha BSC | 3:1 | ||||
| 27. Round | 01/04/2000 | Hertha BSC | - | FC Schalke 04 | 2:1 | |
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| 28. Round | 08/04/2000 | Hertha BSC | - | Eintracht Frankfurt | 1:0 | ||||
| 29. Round | 11/04/2000 | 1. FC Kaiserslautern | - | Hertha BSC | 1:2 | ||||
| 30. Round | 14/04/2000 | Hertha BSC | - | VfL Wolfsburg | 0:0 | |
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| 31. Round | 22/04/2000 | SSV Ulm 1846 | - | Hertha BSC | 0:1 | ||||
| 32. Round | 28/04/2000 | Hertha BSC | - | SC Freiburg | 0:0 | ||||
| 33. Round | 13/05/2000 | TSV 1860 München | - | Hertha BSC | 2:1 |
Hungary
