1st(1st leg) Nistru Otaci - SV Austria Salzburg 2:6 (1:0)
2nd (2nd leg) SV Austria Salzburg - Nistru Otaci 1:1 (1:1)
1st(1st leg): 01/07/2000 2nd (2nd leg): 08/07/2000 Winner: SV Austria Salzburg
1st(1st leg) Nea Salamina - Austria Wien 1:0 (1:0)
2nd (2nd leg) Austria Wien - Nea Salamina 3:0 (1:0)
1st(1st leg): 01/07/2000 2nd (2nd leg): 08/07/2000 Winner: Austria Wien
1st(1st leg) Lombard FC Tatabanya - HNK Cibalia 3:2 (1:1)
2nd (2nd leg) HNK Cibalia - Lombard FC Tatabanya 0:0 (0:0)
1st(1st leg): 01/07/2000 14:15 2nd (2nd leg): 08/07/2000 17:00 Winner: Lombard FC Tatabanya
1st(1st leg) Zenit St. Petersburg - NK Primorje 3:0 (2:0)
2nd (2nd leg) NK Primorje - Zenit St. Petersburg 1:3 (0:2)
1st(1st leg): 01/07/2000 15:00 2nd (2nd leg): 09/07/2000 17:00 Winner: Zenit St. Petersburg
1st(1st leg) Stabæk IF - AJ Auxerre 0:2 (0:0)
2nd (2nd leg) AJ Auxerre - Stabæk IF 3:0 dec.
1st(1st leg): 01/07/2000 15:00 2nd (2nd leg): 08/07/2000 19:00 Winner: AJ Auxerre
1st(1st leg) Chmel Blsany - Dnepr Mogilev 6:2 (2:1)
2nd (2nd leg) Dnepr Mogilev - Chmel Blsany 0:2 (0:0)
1st(1st leg): 01/07/2000 15:30 2nd (2nd leg): 08/07/2000 15:00 Winner: Chmel Blsany
1st(1st leg) Neuchâtel Xamax FC - VfB Stuttgart 1:6 (0:3)
2nd (2nd leg) VfB Stuttgart - Neuchâtel Xamax FC 4:1 (1:0)
1st(1st leg): 01/07/2000 16:00 2nd (2nd leg): 09/07/2000 17:00 Winner: VfB Stuttgart
1st(1st leg) Zagłębie Lubin - Slaven Belupo 1:1 (1:0)
2nd (2nd leg) Slaven Belupo - Zagłębie Lubin 0:0 (0:0)
1st(1st leg): 01/07/2000 16:00 2nd (2nd leg): 08/07/2000 17:00 Winner: Slaven Belupo
1st(1st leg) FK Pelister - Västra Frölunda 3:1 (0:1)
2nd (2nd leg) Västra Frölunda - FK Pelister 0:0 (0:0)
1st(1st leg): 01/07/2000 16:30 2nd (2nd leg): 08/07/2000 16:00 Winner: FK Pelister
1st(1st leg) LASK Linz - FC Marila Příbram 1:1 (0:1)
2nd (2nd leg) FC Marila Příbram - LASK Linz 3:2 (1:1)
1st(1st leg): 01/07/2000 17:00 2nd (2nd leg): 09/07/2000 16:30 Winner: FC Marila Příbram
1st(1st leg) CS Sedan - ÍF Leiftur 3:0 (2:0)
2nd (2nd leg) ÍF Leiftur - CS Sedan 2:3 (0:3)
1st(1st leg): 01/07/2000 19:00 2nd (2nd leg): 08/07/2000 16:00 Winner: CS Sedan
1st(1st leg) AC Perugia - Standard Liège 1:2 (0:1)
2nd (2nd leg) Standard Liège - AC Perugia 1:1 (0:1)
1st(1st leg): 01/07/2000 19:45 2nd (2nd leg): 08/07/2000 19:00 Winner: Standard Liège
1st(1st leg) RCD Mallorca - Ceahlăul Piatra Neamt 2:1 (2:1)
2nd (2nd leg) Ceahlăul Piatra Neamt - RCD Mallorca 3:1 (1:1)
1st(1st leg): 01/07/2000 20:00 2nd (2nd leg): 08/07/2000 15:00 Winner: Ceahlăul Piatra Neamt
1st(1st leg) FC Dinaburg - Aalborg BK 0:0 (0:0)
2nd (2nd leg) Aalborg BK - FC Dinaburg 1:0 (0:0)
1st(1st leg): 02/07/2000 15:00 2nd (2nd leg): 09/07/2000 14:00 Winner: Aalborg BK
1st(1st leg) FK Atlantas - Bradford City 1:3 (1:2)
2nd (2nd leg) Bradford City - FK Atlantas 4:1 (2:0)
1st(1st leg): 02/07/2000 15:00 2nd (2nd leg): 09/07/2000 15:00 Winner: Bradford City
1st(1st leg) FC Velbazhd 1919 Kyustendil - Sigma Olomouc 2:0 (1:0)
2nd (2nd leg) Sigma Olomouc - FC Velbazhd 1919 Kyustendil 8:0 (2:0)
1st(1st leg): 02/07/2000 16:00 2nd (2nd leg): 08/07/2000 17:00 Winner: Sigma Olomouc