| Preliminary Gr. H | 20/09/1999 | Hertha BSC | - | Chelsea FC | 2:1 |  |
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| Preliminary Gr. H | 27/09/1999 | AC Milan | - | Hertha BSC | 1:1 | ||||
| Preliminary Gr. H | 19/10/1999 | Hertha BSC | - | AC Milan | 1:0 | ||||
| Preliminary Gr. H | 25/10/1999 | Hertha BSC | - | Galatasaray | 1:4 | ||||
| Preliminary Gr. H | 02/11/1999 | Chelsea FC | - | Hertha BSC | 2:0 | ||||
| Intermediate Gr. A | 22/11/1999 | Hertha BSC | - | FC Barcelona | 1:1 | ||||
| Intermediate Gr. A | 07/12/1999 | FC Porto | - | Hertha BSC | 1:0 | ||||
| Intermediate Gr. A | 29/02/2000 | Hertha BSC | - | AC Sparta Praha | 1:1 | ||||
| Intermediate Gr. A | 14/03/2000 | FC Barcelona | - | Hertha BSC | 3:1 | ||||
| Intermediate Gr. A | 20/03/2000 | Hertha BSC | - | FC Porto | 0:1 |
Netherlands