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| H | Montpellier HSC | - | Hamburger SV | 1:1 (1:0) | ||
| R | Hamburger SV | - | Montpellier HSC | 0:3 (1:0, 1:1, 1:1) i.E. | ||
| H: 10.08.1999 19:00 | R: 24.08.1999 18:00 | Sieger: Montpellier HSC | ||||
| H | Juventus | - | Stade Rennais | 2:0 (1:0) | ||
| R | Stade Rennais | - | Juventus | 2:2 (1:1) | ||
| H: 10.08.1999 20:45 | R: 24.08.1999 20:45 | Sieger: Juventus | ||||
| H | West Ham United | - | FC Metz | 0:1 (0:1) | ||
| R | FC Metz | - | West Ham United | 1:3 (0:2) | ||
| H: 10.08.1999 20:45 | R: 24.08.1999 20:00 | Sieger: West Ham United | ||||
