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| U | Rostselmash Rostov | - | Juventus | 0:4 (0:1) | ||
| R | Juventus | - | Rostselmash Rostov | 5:1 (1:1) | ||
| U: 28.07.1999 16:00 | R: 04.08.1999 20:45 | Winnaars: Juventus | ||||
| U | Trabzonspor | - | Hamburger SV | 2:2 (0:0) | ||
| R | Hamburger SV | - | Trabzonspor | 4:1 (1:0) | ||
| U: 28.07.1999 19:00 | R: 04.08.1999 20:00 | Winnaars: Hamburger SV | ||||
| U | Stade Rennais | - | Austria Wien | 2:0 (0:0) | ||
| R | Austria Wien | - | Stade Rennais | 2:2 (2:0) | ||
| U: 28.07.1999 20:00 | R: 04.08.1999 19:00 | Winnaars: Stade Rennais | ||||
| U | MSV Duisburg | - | Montpellier HSC | 1:1 (1:1) | ||
| R | Montpellier HSC | - | MSV Duisburg | 3:0 (1:0) | ||
| U: 28.07.1999 20:00 | R: 04.08.1999 20:00 | Winnaars: Montpellier HSC | ||||
| U | FC Metz | - | Polonia Warszawa | 5:1 (2:0) | ||
| R | Polonia Warszawa | - | FC Metz | 1:1 (0:0) | ||
| U: 28.07.1999 20:00 | R: 04.08.1999 16:00 | Winnaars: FC Metz | ||||
| U | West Ham United | - | sc Heerenveen | 1:0 (1:0) | ||
| R | sc Heerenveen | - | West Ham United | 0:1 (0:1) | ||
| U: 28.07.1999 20:45 | R: 04.08.1999 20:00 | Winnaars: West Ham United | ||||
