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| 1st(1st leg) | Ceahlăul Piatra Neamt | - | Austria Wien | 2:2 (0:2) | ||
| 2nd (2nd leg) | Austria Wien | - | Ceahlăul Piatra Neamt | 3:0 (1:0) | ||
| 1st(1st leg): 15/07/2000 15:00 | 2nd (2nd leg): 22/07/2000 18:30 | Winner: Austria Wien | ||||
| 1st(1st leg) | Chmel Blsany | - | PS Kalamata | 5:0 (2:0) | ||
| 2nd (2nd leg) | PS Kalamata | - | Chmel Blsany | 0:3 (0:1) | ||
| 1st(1st leg): 15/07/2000 15:30 | 2nd (2nd leg): 22/07/2000 19:00 | Winner: Chmel Blsany | ||||
| 1st(1st leg) | Slaven Belupo | - | Sigma Olomouc | 1:1 (1:1) | ||
| 2nd (2nd leg) | Sigma Olomouc | - | Slaven Belupo | 2:0 (0:0) | ||
| 1st(1st leg): 15/07/2000 16:00 | 2nd (2nd leg): 22/07/2000 15:30 | Winner: Sigma Olomouc | ||||
| 1st(1st leg) | Zenit St. Petersburg | - | Lombard FC Tatabanya | 2:1 (0:1) | ||
| 2nd (2nd leg) | Lombard FC Tatabanya | - | Zenit St. Petersburg | 1:2 (0:0) | ||
| 1st(1st leg): 15/07/2000 16:00 | 2nd (2nd leg): 22/07/2000 17:00 | Winner: Zenit St. Petersburg | ||||
| 1st(1st leg) | Standard Liège | - | SV Austria Salzburg | 3:1 (1:1) | ||
| 2nd (2nd leg) | SV Austria Salzburg | - | Standard Liège | 1:1 (0:1) | ||
| 1st(1st leg): 15/07/2000 19:00 | 2nd (2nd leg): 22/07/2000 17:00 | Winner: Standard Liège | ||||
| 1st(1st leg) | CS Sedan | - | VfL Wolfsburg | 0:0 (0:0) | ||
| 2nd (2nd leg) | VfL Wolfsburg | - | CS Sedan | 2:1 (1:0) | ||
| 1st(1st leg): 15/07/2000 19:30 | 2nd (2nd leg): 22/07/2000 17:15 | Winner: VfL Wolfsburg | ||||
| 1st(1st leg) | RC Lens | - | VfB Stuttgart | 2:1 (1:0) | ||
| 2nd (2nd leg) | VfB Stuttgart | - | RC Lens | 1:0 (1:0) | ||
| 1st(1st leg): 15/07/2000 19:30 | 2nd (2nd leg): 22/07/2000 17:15 | Winner: VfB Stuttgart | ||||
| 1st(1st leg) | RC Celta | - | FK Pelister | 3:0 (1:0) | ||
| 2nd (2nd leg) | FK Pelister | - | RC Celta | 1:2 (0:0) | ||
| 1st(1st leg): 15/07/2000 20:00 | 2nd (2nd leg): 22/07/2000 16:30 | Winner: RC Celta | ||||
| 1st(1st leg) | Aalborg BK | - | Udinese Calcio | 0:2 (0:0) | ||
| 2nd (2nd leg) | Udinese Calcio | - | Aalborg BK | 1:2 (1:1) | ||
| 1st(1st leg): 16/07/2000 14:00 | 2nd (2nd leg): 22/07/2000 19:45 | Winner: Udinese Calcio | ||||
| 1st(1st leg) | Bradford City | - | RKC Waalwijk | 2:0 (0:0) | ||
| 2nd (2nd leg) | RKC Waalwijk | - | Bradford City | 0:1 (0:0) | ||
| 1st(1st leg): 16/07/2000 15:00 | 2nd (2nd leg): 22/07/2000 18:30 | Winner: Bradford City | ||||
| 1st(1st leg) | FC Marila Příbram | - | Aston Villa | 0:0 (0:0) | ||
| 2nd (2nd leg) | Aston Villa | - | FC Marila Příbram | 3:1 (1:1) | ||
| 1st(1st leg): 16/07/2000 16:00 | 2nd (2nd leg): 22/07/2000 14:00 | Winner: Aston Villa | ||||
| 1st(1st leg) | Rostselmash Rostov | - | AJ Auxerre | 0:2 (0:1) | ||
| 2nd (2nd leg) | AJ Auxerre | - | Rostselmash Rostov | 3:1 (3:0) | ||
| 1st(1st leg): 16/07/2000 16:00 | 2nd (2nd leg): 22/07/2000 19:30 | Winner: AJ Auxerre | ||||
