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| U | Nistru Otaci | - | SV Austria Salzburg | 2:6 (1:0) | ||
| R | SV Austria Salzburg | - | Nistru Otaci | 1:1 (1:1) | ||
| U: 01.07.2000 | R: 08.07.2000 | Winnaars: SV Austria Salzburg | ||||
| U | Nea Salamina | - | Austria Wien | 1:0 (1:0) | ||
| R | Austria Wien | - | Nea Salamina | 3:0 (1:0) | ||
| U: 01.07.2000 | R: 08.07.2000 | Winnaars: Austria Wien | ||||
| U | Lombard FC Tatabanya | - | HNK Cibalia | 3:2 (1:1) | ||
| R | HNK Cibalia | - | Lombard FC Tatabanya | 0:0 (0:0) | ||
| U: 01.07.2000 15:15 | R: 08.07.2000 18:00 | Winnaars: Lombard FC Tatabanya | ||||
| U | Zenit St. Petersburg | - | NK Primorje | 3:0 (2:0) | ||
| R | NK Primorje | - | Zenit St. Petersburg | 1:3 (0:2) | ||
| U: 01.07.2000 16:00 | R: 09.07.2000 18:00 | Winnaars: Zenit St. Petersburg | ||||
| U | Stabæk IF | - | AJ Auxerre | 0:2 (0:0) | ||
| R | AJ Auxerre | - | Stabæk IF | 3:0 Toeg. | ||
| U: 01.07.2000 16:00 | R: 08.07.2000 20:00 | Winnaars: AJ Auxerre | ||||
| U | Chmel Blsany | - | Dnepr Mogilev | 6:2 (2:1) | ||
| R | Dnepr Mogilev | - | Chmel Blsany | 0:2 (0:0) | ||
| U: 01.07.2000 16:30 | R: 08.07.2000 16:00 | Winnaars: Chmel Blsany | ||||
| U | Neuchâtel Xamax FC | - | VfB Stuttgart | 1:6 (0:3) | ||
| R | VfB Stuttgart | - | Neuchâtel Xamax FC | 4:1 (1:0) | ||
| U: 01.07.2000 17:00 | R: 09.07.2000 18:00 | Winnaars: VfB Stuttgart | ||||
| U | Zagłębie Lubin | - | Slaven Belupo | 1:1 (1:0) | ||
| R | Slaven Belupo | - | Zagłębie Lubin | 0:0 (0:0) | ||
| U: 01.07.2000 17:00 | R: 08.07.2000 18:00 | Winnaars: Slaven Belupo | ||||
| U | FK Pelister | - | Västra Frölunda | 3:1 (0:1) | ||
| R | Västra Frölunda | - | FK Pelister | 0:0 (0:0) | ||
| U: 01.07.2000 17:30 | R: 08.07.2000 17:00 | Winnaars: FK Pelister | ||||
| U | LASK Linz | - | FC Marila Příbram | 1:1 (0:1) | ||
| R | FC Marila Příbram | - | LASK Linz | 3:2 (1:1) | ||
| U: 01.07.2000 18:00 | R: 09.07.2000 17:30 | Winnaars: FC Marila Příbram | ||||
| U | CS Sedan | - | ÍF Leiftur | 3:0 (2:0) | ||
| R | ÍF Leiftur | - | CS Sedan | 2:3 (0:3) | ||
| U: 01.07.2000 20:00 | R: 08.07.2000 17:00 | Winnaars: CS Sedan | ||||
| U | AC Perugia | - | Standard Luik | 1:2 (0:1) | ||
| R | Standard Luik | - | AC Perugia | 1:1 (0:1) | ||
| U: 01.07.2000 20:45 | R: 08.07.2000 20:00 | Winnaars: Standard Luik | ||||
| U | RCD Mallorca | - | Ceahlăul Piatra Neamt | 2:1 (2:1) | ||
| R | Ceahlăul Piatra Neamt | - | RCD Mallorca | 3:1 (1:1) | ||
| U: 01.07.2000 21:00 | R: 08.07.2000 16:00 | Winnaars: Ceahlăul Piatra Neamt | ||||
| U | FC Dinaburg | - | Aalborg BK | 0:0 (0:0) | ||
| R | Aalborg BK | - | FC Dinaburg | 1:0 (0:0) | ||
| U: 02.07.2000 16:00 | R: 09.07.2000 15:00 | Winnaars: Aalborg BK | ||||
| U | FK Atlantas | - | Bradford City | 1:3 (1:2) | ||
| R | Bradford City | - | FK Atlantas | 4:1 (2:0) | ||
| U: 02.07.2000 16:00 | R: 09.07.2000 16:00 | Winnaars: Bradford City | ||||
| U | FC Velbazhd 1919 Kyustendil | - | Sigma Olomouc | 2:0 (1:0) | ||
| R | Sigma Olomouc | - | FC Velbazhd 1919 Kyustendil | 8:0 (2:0) | ||
| U: 02.07.2000 17:00 | R: 08.07.2000 18:00 | Winnaars: Sigma Olomouc | ||||
