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| U | Sigma Olomouc | - | Chmel Blsany | 3:1 (2:1) | ||
| R | Chmel Blsany | - | Sigma Olomouc | 0:0 (0:0) | ||
| U: 26.07.2000 16:30 | R: 02.08.2000 16:30 | Winnaars: Sigma Olomouc | ||||
| U | Zenit St. Petersburg | - | Bradford City | 1:0 (1:0) | ||
| R | Bradford City | - | Zenit St. Petersburg | 0:3 (0:0) | ||
| U: 26.07.2000 17:00 | R: 02.08.2000 20:45 | Winnaars: Zenit St. Petersburg | ||||
| U | VfB Stuttgart | - | Standard Luik | 1:1 (0:0) | ||
| R | Standard Luik | - | VfB Stuttgart | 0:1 (0:1) | ||
| U: 26.07.2000 20:15 | R: 02.08.2000 20:00 | Winnaars: VfB Stuttgart | ||||
| U | Austria Wien | - | Udinese Calcio | 0:1 (0:1) | ||
| R | Udinese Calcio | - | Austria Wien | 2:0 (2:0) | ||
| U: 26.07.2000 20:30 | R: 02.08.2000 21:00 | Winnaars: Udinese Calcio | ||||
| U | AJ Auxerre | - | VfL Wolfsburg | 1:1 (0:1) | ||
| R | VfL Wolfsburg | - | AJ Auxerre | 1:2 (0:1, 1:1) n.v. | ||
| U: 26.07.2000 20:30 | R: 02.08.2000 20:00 | Winnaars: AJ Auxerre | ||||
| U | Celta de Vigo | - | Aston Villa | 1:0 (0:0) | ||
| R | Aston Villa | - | Celta de Vigo | 1:2 (0:1) | ||
| U: 26.07.2000 21:30 | R: 02.08.2000 20:45 | Winnaars: Celta de Vigo | ||||
