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| 1st(1st leg) | Montpellier HSC | - | Hamburger SV | 1:1 (1:0) | ||
| 2nd (2nd leg) | Hamburger SV | - | Montpellier HSC | 0:3 (1:0, 1:1, 1:1) pso | ||
| 1st(1st leg): 10/08/1999 18:00 | 2nd (2nd leg): 24/08/1999 17:00 | Winner: Montpellier HSC | ||||
| 1st(1st leg) | Juventus | - | Stade Rennais | 2:0 (1:0) | ||
| 2nd (2nd leg) | Stade Rennais | - | Juventus | 2:2 (1:1) | ||
| 1st(1st leg): 10/08/1999 19:45 | 2nd (2nd leg): 24/08/1999 19:45 | Winner: Juventus | ||||
| 1st(1st leg) | West Ham United | - | FC Metz | 0:1 (0:1) | ||
| 2nd (2nd leg) | FC Metz | - | West Ham United | 1:3 (0:2) | ||
| 1st(1st leg): 10/08/1999 19:45 | 2nd (2nd leg): 24/08/1999 19:00 | Winner: West Ham United | ||||
