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| 1st(1st leg) | Olympique Lyonnais | - | Maribor Teatanic | 0:1 (0:0) | ||
| 2nd (2nd leg) | Maribor Teatanic | - | Olympique Lyonnais | 2:0 (2:0) | ||
| 1st(1st leg): 10/08/1999 19:30 | 2nd (2nd leg): 25/08/1999 19:30 | Winner: Maribor Teatanic | ||||
| 1st(1st leg) | Spartak Moskva | - | Partizan | 2:0 (1:0) | ||
| 2nd (2nd leg) | Partizan | - | Spartak Moskva | 1:3 (0:1) | ||
| 1st(1st leg): 11/08/1999 17:00 | 2nd (2nd leg): 25/08/1999 19:15 | Winner: Spartak Moskva | ||||
| 1st(1st leg) | FK Teplice | - | Borussia Dortmund | 0:1 (0:0) | ||
| 2nd (2nd leg) | Borussia Dortmund | - | FK Teplice | 1:0 (0:0) | ||
| 1st(1st leg): 11/08/1999 17:00 | 2nd (2nd leg): 25/08/1999 19:30 | Winner: Borussia Dortmund | ||||
| 1st(1st leg) | Aalborg BK | - | Dinamo Kiev | 1:2 (0:2) | ||
| 2nd (2nd leg) | Dinamo Kiev | - | Aalborg BK | 2:2 (0:1) | ||
| 1st(1st leg): 11/08/1999 17:30 | 2nd (2nd leg): 25/08/1999 17:00 | Winner: Dinamo Kiev | ||||
| 1st(1st leg) | FC Zimbru | - | PSV Eindhoven | 0:0 (0:0) | ||
| 2nd (2nd leg) | PSV Eindhoven | - | FC Zimbru | 2:0 (2:0) | ||
| 1st(1st leg): 11/08/1999 18:30 | 2nd (2nd leg): 25/08/1999 19:00 | Winner: PSV Eindhoven | ||||
| 1st(1st leg) | Rapid Wien | - | Galatasaray | 0:3 (0:2) | ||
| 2nd (2nd leg) | Galatasaray | - | Rapid Wien | 1:0 (0:0) | ||
| 1st(1st leg): 11/08/1999 18:30 | 2nd (2nd leg): 25/08/1999 19:30 | Winner: Galatasaray | ||||
| 1st(1st leg) | Hapoel Haifa | - | Valencia CF | 0:2 (0:0) | ||
| 2nd (2nd leg) | Valencia CF | - | Hapoel Haifa | 2:0 (0:0) | ||
| 1st(1st leg): 11/08/1999 18:30 | 2nd (2nd leg): 25/08/1999 21:00 | Winner: Valencia CF | ||||
| 1st(1st leg) | Molde FK | - | RCD Mallorca | 0:0 (0:0) | ||
| 2nd (2nd leg) | RCD Mallorca | - | Molde FK | 1:1 (1:0) | ||
| 1st(1st leg): 11/08/1999 19:00 | 2nd (2nd leg): 25/08/1999 20:30 | Winner: Molde FK | ||||
| 1st(1st leg) | AEK Athen | - | AIK Solna | 0:0 (0:0) | ||
| 2nd (2nd leg) | AIK Solna | - | AEK Athen | 1:0 (0:0) | ||
| 1st(1st leg): 11/08/1999 19:15 | 2nd (2nd leg): 25/08/1999 18:00 | Winner: AIK Solna | ||||
| 1st(1st leg) | Croatia Zagreb | - | MTK Hungaria | 0:0 (0:0) | ||
| 2nd (2nd leg) | MTK Hungaria | - | Croatia Zagreb | 0:2 (0:0) | ||
| 1st(1st leg): 11/08/1999 19:15 | 2nd (2nd leg): 25/08/1999 19:15 | Winner: Croatia Zagreb | ||||
| 1st(1st leg) | ACF Fiorentina | - | Widzew Łódź | 3:1 (1:0) | ||
| 2nd (2nd leg) | Widzew Łódź | - | ACF Fiorentina | 0:2 (0:1) | ||
| 1st(1st leg): 11/08/1999 19:45 | 2nd (2nd leg): 25/08/1999 17:00 | Winner: ACF Fiorentina | ||||
| 1st(1st leg) | Brøndby IF | - | Boavista | 1:2 (0:1) | ||
| 2nd (2nd leg) | Boavista | - | Brøndby IF | 4:2 (1:0, 1:2, 4:2) aet | ||
| 1st(1st leg): 11/08/1999 19:45 | 2nd (2nd leg): 25/08/1999 21:00 | Winner: Boavista | ||||
| 1st(1st leg) | Hertha BSC | - | Anorthosis Famagusta | 2:0 (1:0) | ||
| 2nd (2nd leg) | Anorthosis Famagusta | - | Hertha BSC | 0:0 (0:0) | ||
| 1st(1st leg): 11/08/1999 19:45 | 2nd (2nd leg): 25/08/1999 17:00 | Winner: Hertha BSC | ||||
| 1st(1st leg) | Chelsea FC | - | Skonto FC | 3:0 (0:0) | ||
| 2nd (2nd leg) | Skonto FC | - | Chelsea FC | 0:0 (0:0) | ||
| 1st(1st leg): 11/08/1999 20:05 | 2nd (2nd leg): 25/08/1999 17:30 | Winner: Chelsea FC | ||||
| 1st(1st leg) | Rangers FC | - | Parma AC | 2:0 (1:0) | ||
| 2nd (2nd leg) | Parma AC | - | Rangers FC | 1:0 (0:0) | ||
| 1st(1st leg): 11/08/1999 20:05 | 2nd (2nd leg): 25/08/1999 20:00 | Winner: Rangers FC | ||||
| 1st(1st leg) | Sturm Graz | - | Servette FC | 2:1 (2:1) | ||
| 2nd (2nd leg) | Servette FC | - | Sturm Graz | 2:2 (0:0) | ||
| 1st(1st leg): 11/08/1999 20:15 | 2nd (2nd leg): 25/08/1999 19:45 | Winner: Sturm Graz | ||||
