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| 1st(1st leg) | West Ham United | - | Jokerit Helsinki | 1:0 (1:0) | ||
| 2nd (2nd leg) | Jokerit Helsinki | - | West Ham United | 1:1 (1:0) | ||
| 1st(1st leg): 17/07/1999 15:00 | 2nd (2nd leg): 24/07/1999 17:00 | Winner: West Ham United | ||||
| 1st(1st leg) | Polonia Warszawa | - | Budapesti Vasas | 2:0 (1:0) | ||
| 2nd (2nd leg) | Budapesti Vasas | - | Polonia Warszawa | 1:2 (0:0) | ||
| 1st(1st leg): 17/07/1999 15:00 | 2nd (2nd leg): 24/07/1999 19:00 | Winner: Polonia Warszawa | ||||
| 1st(1st leg) | Austria Lustenau | - | Stade Rennais | 2:1 (1:0) | ||
| 2nd (2nd leg) | Stade Rennais | - | Austria Lustenau | 1:0 (1:0) | ||
| 1st(1st leg): 17/07/1999 18:00 | 2nd (2nd leg): 24/07/1999 17:00 | Winner: Stade Rennais | ||||
| 1st(1st leg) | Trabzonspor | - | AC Perugia | 1:2 (0:1) | ||
| 2nd (2nd leg) | AC Perugia | - | Trabzonspor | 0:3 dec. | ||
| 1st(1st leg): 17/07/1999 18:00 | 2nd (2nd leg): 24/07/1999 19:45 | Winner: Trabzonspor | ||||
| 1st(1st leg) | Kocaelispor | - | MSV Duisburg | 0:3 (0:1) | ||
| 2nd (2nd leg) | MSV Duisburg | - | Kocaelispor | 0:0 (0:0) | ||
| 1st(1st leg): 17/07/1999 18:30 | 2nd (2nd leg): 24/07/1999 17:00 | Winner: MSV Duisburg | ||||
| 1st(1st leg) | sc Heerenveen | - | Hammarby IF | 2:0 (1:0) | ||
| 2nd (2nd leg) | Hammarby IF | - | sc Heerenveen | 0:2 (0:1) | ||
| 1st(1st leg): 17/07/1999 19:00 | 2nd (2nd leg): 24/07/1999 16:00 | Winner: sc Heerenveen | ||||
| 1st(1st leg) | Sint-Truidense VV | - | Austria Wien | 0:2 (0:1) | ||
| 2nd (2nd leg) | Austria Wien | - | Sint-Truidense VV | 1:2 (0:2) | ||
| 1st(1st leg): 17/07/1999 19:00 | 2nd (2nd leg): 24/07/1999 18:30 | Winner: Austria Wien | ||||
| 1st(1st leg) | NK Varteks | - | Rostselmash Rostov | 1:2 (1:1) | ||
| 2nd (2nd leg) | Rostselmash Rostov | - | NK Varteks | 0:1 (0:0) | ||
| 1st(1st leg): 17/07/1999 19:00 | 2nd (2nd leg): 24/07/1999 15:00 | Winner: Rostselmash Rostov | ||||
| 1st(1st leg) | Sporting Lokeren | - | FC Metz | 1:2 (0:0) | ||
| 2nd (2nd leg) | FC Metz | - | Sporting Lokeren | 0:1 (0:1) | ||
| 1st(1st leg): 17/07/1999 19:00 | 2nd (2nd leg): 24/07/1999 19:00 | Winner: FC Metz | ||||
| 1st(1st leg) | Espanyol Barcelona | - | Montpellier HSC | 0:2 (0:1) | ||
| 2nd (2nd leg) | Montpellier HSC | - | Espanyol Barcelona | 2:1 (1:0) | ||
| 1st(1st leg): 17/07/1999 19:00 | 2nd (2nd leg): 24/07/1999 19:00 | Winner: Montpellier HSC | ||||
| 1st(1st leg) | Ceahlăul Piatra Neamt | - | Juventus | 1:1 (1:0) | ||
| 2nd (2nd leg) | Juventus | - | Ceahlăul Piatra Neamt | 0:0 (0:0) | ||
| 1st(1st leg): 18/07/1999 16:00 | 2nd (2nd leg): 24/07/1999 19:45 | Winner: Juventus | ||||
| 1st(1st leg) | Hamburger SV | - | FC Basel 1893 | 0:1 (0:1) | ||
| 2nd (2nd leg) | FC Basel 1893 | - | Hamburger SV | 2:3 (0:2) | ||
| 1st(1st leg): 18/07/1999 17:15 | 2nd (2nd leg): 24/07/1999 15:45 | Winner: Hamburger SV | ||||
