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| 1st(1st leg) | Sigma Olomouc | - | Chmel Blsany | 3:1 (2:1) | ||
| 2nd (2nd leg) | Chmel Blsany | - | Sigma Olomouc | 0:0 (0:0) | ||
| 1st(1st leg): 26/07/2000 15:30 | 2nd (2nd leg): 02/08/2000 15:30 | Winner: Sigma Olomouc | ||||
| 1st(1st leg) | Zenit St. Petersburg | - | Bradford City | 1:0 (1:0) | ||
| 2nd (2nd leg) | Bradford City | - | Zenit St. Petersburg | 0:3 (0:0) | ||
| 1st(1st leg): 26/07/2000 16:00 | 2nd (2nd leg): 02/08/2000 19:45 | Winner: Zenit St. Petersburg | ||||
| 1st(1st leg) | VfB Stuttgart | - | Standard Liège | 1:1 (0:0) | ||
| 2nd (2nd leg) | Standard Liège | - | VfB Stuttgart | 0:1 (0:1) | ||
| 1st(1st leg): 26/07/2000 19:15 | 2nd (2nd leg): 02/08/2000 19:00 | Winner: VfB Stuttgart | ||||
| 1st(1st leg) | Austria Wien | - | Udinese Calcio | 0:1 (0:1) | ||
| 2nd (2nd leg) | Udinese Calcio | - | Austria Wien | 2:0 (2:0) | ||
| 1st(1st leg): 26/07/2000 19:30 | 2nd (2nd leg): 02/08/2000 20:00 | Winner: Udinese Calcio | ||||
| 1st(1st leg) | AJ Auxerre | - | VfL Wolfsburg | 1:1 (0:1) | ||
| 2nd (2nd leg) | VfL Wolfsburg | - | AJ Auxerre | 1:2 (0:1, 1:1) aet | ||
| 1st(1st leg): 26/07/2000 19:30 | 2nd (2nd leg): 02/08/2000 19:00 | Winner: AJ Auxerre | ||||
| 1st(1st leg) | RC Celta | - | Aston Villa | 1:0 (0:0) | ||
| 2nd (2nd leg) | Aston Villa | - | RC Celta | 1:2 (0:1) | ||
| 1st(1st leg): 26/07/2000 20:30 | 2nd (2nd leg): 02/08/2000 19:45 | Winner: RC Celta | ||||
