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| I | Rostselmash Rostov | - | Juventus | 0:4 (0:1) | ||
| V | Juventus | - | Rostselmash Rostov | 5:1 (1:1) | ||
| I: 28.07.1999 16:00 | V: 04.08.1999 20:45 | Campeones: Juventus | ||||
| I | Trabzonspor | - | Hamburgo | 2:2 (0:0) | ||
| V | Hamburgo | - | Trabzonspor | 4:1 (1:0) | ||
| I: 28.07.1999 19:00 | V: 04.08.1999 20:00 | Campeones: Hamburgo | ||||
| I | Rennes | - | Austria Wien | 2:0 (0:0) | ||
| V | Austria Wien | - | Rennes | 2:2 (2:0) | ||
| I: 28.07.1999 20:00 | V: 04.08.1999 19:00 | Campeones: Rennes | ||||
| I | MSV Duisburg | - | Montpellier | 1:1 (1:1) | ||
| V | Montpellier | - | MSV Duisburg | 3:0 (1:0) | ||
| I: 28.07.1999 20:00 | V: 04.08.1999 20:00 | Campeones: Montpellier | ||||
| I | FC Metz | - | Polonia Warszawa | 5:1 (2:0) | ||
| V | Polonia Warszawa | - | FC Metz | 1:1 (0:0) | ||
| I: 28.07.1999 20:00 | V: 04.08.1999 16:00 | Campeones: FC Metz | ||||
| I | West Ham United | - | sc Heerenveen | 1:0 (1:0) | ||
| V | sc Heerenveen | - | West Ham United | 0:1 (0:1) | ||
| I: 28.07.1999 20:45 | V: 04.08.1999 20:00 | Campeones: West Ham United | ||||
