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| U | Ceahlăul Piatra Neamt | - | Austria Wien | 2:2 (0:2) | ||
| R | Austria Wien | - | Ceahlăul Piatra Neamt | 3:0 (1:0) | ||
| U: 15.07.2000 16:00 | R: 22.07.2000 19:30 | Winnaars: Austria Wien | ||||
| U | Chmel Blsany | - | PS Kalamata | 5:0 (2:0) | ||
| R | PS Kalamata | - | Chmel Blsany | 0:3 (0:1) | ||
| U: 15.07.2000 16:30 | R: 22.07.2000 20:00 | Winnaars: Chmel Blsany | ||||
| U | Slaven Belupo | - | Sigma Olomouc | 1:1 (1:1) | ||
| R | Sigma Olomouc | - | Slaven Belupo | 2:0 (0:0) | ||
| U: 15.07.2000 17:00 | R: 22.07.2000 16:30 | Winnaars: Sigma Olomouc | ||||
| U | Zenit St. Petersburg | - | Lombard FC Tatabanya | 2:1 (0:1) | ||
| R | Lombard FC Tatabanya | - | Zenit St. Petersburg | 1:2 (0:0) | ||
| U: 15.07.2000 17:00 | R: 22.07.2000 18:00 | Winnaars: Zenit St. Petersburg | ||||
| U | Standard Luik | - | SV Austria Salzburg | 3:1 (1:1) | ||
| R | SV Austria Salzburg | - | Standard Luik | 1:1 (0:1) | ||
| U: 15.07.2000 20:00 | R: 22.07.2000 18:00 | Winnaars: Standard Luik | ||||
| U | CS Sedan | - | VfL Wolfsburg | 0:0 (0:0) | ||
| R | VfL Wolfsburg | - | CS Sedan | 2:1 (1:0) | ||
| U: 15.07.2000 20:30 | R: 22.07.2000 18:15 | Winnaars: VfL Wolfsburg | ||||
| U | RC Lens | - | VfB Stuttgart | 2:1 (1:0) | ||
| R | VfB Stuttgart | - | RC Lens | 1:0 (1:0) | ||
| U: 15.07.2000 20:30 | R: 22.07.2000 18:15 | Winnaars: VfB Stuttgart | ||||
| U | Celta de Vigo | - | FK Pelister | 3:0 (1:0) | ||
| R | FK Pelister | - | Celta de Vigo | 1:2 (0:0) | ||
| U: 15.07.2000 21:00 | R: 22.07.2000 17:30 | Winnaars: Celta de Vigo | ||||
| U | Aalborg BK | - | Udinese Calcio | 0:2 (0:0) | ||
| R | Udinese Calcio | - | Aalborg BK | 1:2 (1:1) | ||
| U: 16.07.2000 15:00 | R: 22.07.2000 20:45 | Winnaars: Udinese Calcio | ||||
| U | Bradford City | - | RKC Waalwijk | 2:0 (0:0) | ||
| R | RKC Waalwijk | - | Bradford City | 0:1 (0:0) | ||
| U: 16.07.2000 16:00 | R: 22.07.2000 19:30 | Winnaars: Bradford City | ||||
| U | FC Marila Příbram | - | Aston Villa | 0:0 (0:0) | ||
| R | Aston Villa | - | FC Marila Příbram | 3:1 (1:1) | ||
| U: 16.07.2000 17:00 | R: 22.07.2000 15:00 | Winnaars: Aston Villa | ||||
| U | Rostselmash Rostov | - | AJ Auxerre | 0:2 (0:1) | ||
| R | AJ Auxerre | - | Rostselmash Rostov | 3:1 (3:0) | ||
| U: 16.07.2000 17:00 | R: 22.07.2000 20:30 | Winnaars: AJ Auxerre | ||||
