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| 1st(1st leg) | Rostselmash Rostov | - | Juventus | 0:4 (0:1) | ||
| 2nd (2nd leg) | Juventus | - | Rostselmash Rostov | 5:1 (1:1) | ||
| 1st(1st leg): 28/07/1999 15:00 | 2nd (2nd leg): 04/08/1999 19:45 | Winner: Juventus | ||||
| 1st(1st leg) | Trabzonspor | - | Hamburger SV | 2:2 (0:0) | ||
| 2nd (2nd leg) | Hamburger SV | - | Trabzonspor | 4:1 (1:0) | ||
| 1st(1st leg): 28/07/1999 18:00 | 2nd (2nd leg): 04/08/1999 19:00 | Winner: Hamburger SV | ||||
| 1st(1st leg) | Stade Rennais | - | Austria Wien | 2:0 (0:0) | ||
| 2nd (2nd leg) | Austria Wien | - | Stade Rennais | 2:2 (2:0) | ||
| 1st(1st leg): 28/07/1999 19:00 | 2nd (2nd leg): 04/08/1999 18:00 | Winner: Stade Rennais | ||||
| 1st(1st leg) | MSV Duisburg | - | Montpellier HSC | 1:1 (1:1) | ||
| 2nd (2nd leg) | Montpellier HSC | - | MSV Duisburg | 3:0 (1:0) | ||
| 1st(1st leg): 28/07/1999 19:00 | 2nd (2nd leg): 04/08/1999 19:00 | Winner: Montpellier HSC | ||||
| 1st(1st leg) | FC Metz | - | Polonia Warszawa | 5:1 (2:0) | ||
| 2nd (2nd leg) | Polonia Warszawa | - | FC Metz | 1:1 (0:0) | ||
| 1st(1st leg): 28/07/1999 19:00 | 2nd (2nd leg): 04/08/1999 15:00 | Winner: FC Metz | ||||
| 1st(1st leg) | West Ham United | - | sc Heerenveen | 1:0 (1:0) | ||
| 2nd (2nd leg) | sc Heerenveen | - | West Ham United | 0:1 (0:1) | ||
| 1st(1st leg): 28/07/1999 19:45 | 2nd (2nd leg): 04/08/1999 19:00 | Winner: West Ham United | ||||
