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| 1st(1st leg) | Shakhtar Donetsk | - | Levadia Maardu | 4:1 (2:0) | ||
| 2nd (2nd leg) | Levadia Maardu | - | Shakhtar Donetsk | 1:5 (0:2) | ||
| 1st(1st leg): 26/07/2000 16:00 | 2nd (2nd leg): 02/08/2000 16:00 | Winner: Shakhtar Donetsk | ||||
| 1st(1st leg) | FC Zimbru | - | NK Maribor | 2:0 (0:0) | ||
| 2nd (2nd leg) | NK Maribor | - | FC Zimbru | 1:0 (1:0) | ||
| 1st(1st leg): 26/07/2000 16:00 | 2nd (2nd leg): 02/08/2000 19:15 | Winner: FC Zimbru | ||||
| 1st(1st leg) | Haka Valkeakoski | - | FK AŠK Inter Slovnaft Bratislava | 0:0 (0:0) | ||
| 2nd (2nd leg) | FK AŠK Inter Slovnaft Bratislava | - | Haka Valkeakoski | 1:0 (0:0, 0:0) aet | ||
| 1st(1st leg): 26/07/2000 17:00 | 2nd (2nd leg): 02/08/2000 19:00 | Winner: FK AŠK Inter Slovnaft Bratislava | ||||
| 1st(1st leg) | Slavia Praha | - | Shamkir FK | 1:0 (1:0) | ||
| 2nd (2nd leg) | Shamkir FK | - | Slavia Praha | 1:4 (0:1) | ||
| 1st(1st leg): 26/07/2000 17:00 | 2nd (2nd leg): 02/08/2000 14:30 | Winner: Slavia Praha | ||||
| 1st(1st leg) | Brøndby IF | - | KR Reykjavík | 3:1 (1:1) | ||
| 2nd (2nd leg) | KR Reykjavík | - | Brøndby IF | 0:0 (0:0) | ||
| 1st(1st leg): 26/07/2000 17:30 | 2nd (2nd leg): 02/08/2000 19:30 | Winner: Brøndby IF | ||||
| 1st(1st leg) | Helsingborgs IF | - | BATE Borisov | 0:0 (0:0) | ||
| 2nd (2nd leg) | BATE Borisov | - | Helsingborgs IF | 0:3 (0:2) | ||
| 1st(1st leg): 26/07/2000 18:00 | 2nd (2nd leg): 02/08/2000 18:00 | Winner: Helsingborgs IF | ||||
| 1st(1st leg) | Beşiktaş | - | Levski Sofia | 1:0 (0:0) | ||
| 2nd (2nd leg) | Levski Sofia | - | Beşiktaş | 1:1 (0:1) | ||
| 1st(1st leg): 26/07/2000 18:45 | 2nd (2nd leg): 02/08/2000 18:30 | Winner: Beşiktaş | ||||
| 1st(1st leg) | Dinamo Bucureşti | - | Polonia Warszawa | 3:4 (2:2) | ||
| 2nd (2nd leg) | Polonia Warszawa | - | Dinamo Bucureşti | 3:1 (0:1) | ||
| 1st(1st leg): 26/07/2000 19:00 | 2nd (2nd leg): 02/08/2000 19:00 | Winner: Polonia Warszawa | ||||
| 1st(1st leg) | Crvena Zvezda | - | Torpedo Kutaisi | 4:0 (3:0) | ||
| 2nd (2nd leg) | Torpedo Kutaisi | - | Crvena Zvezda | 2:0 (1:0) | ||
| 1st(1st leg): 26/07/2000 19:00 | 2nd (2nd leg): 02/08/2000 16:00 | Winner: Crvena Zvezda | ||||
| 1st(1st leg) | RSC Anderlecht | - | Anorthosis Famagusta | 4:2 (3:1) | ||
| 2nd (2nd leg) | Anorthosis Famagusta | - | RSC Anderlecht | 0:0 (0:0) | ||
| 1st(1st leg): 26/07/2000 19:00 | 2nd (2nd leg): 02/08/2000 18:00 | Winner: RSC Anderlecht | ||||
| 1st(1st leg) | Hajduk Split | - | Dunaferr SE | 0:2 (0:0) | ||
| 2nd (2nd leg) | Dunaferr SE | - | Hajduk Split | 2:2 (1:2) | ||
| 1st(1st leg): 26/07/2000 19:15 | 2nd (2nd leg): 02/08/2000 19:45 | Winner: Dunaferr SE | ||||
| 1st(1st leg) | Sturm Graz | - | Hapoel Tel Aviv | 3:0 (1:0) | ||
| 2nd (2nd leg) | Hapoel Tel Aviv | - | Sturm Graz | 1:2 (0:0) | ||
| 1st(1st leg): 26/07/2000 19:30 | 2nd (2nd leg): 02/08/2000 18:00 | Winner: Sturm Graz | ||||
| 1st(1st leg) | Rangers FC | - | Zalgiris Kaunas | 4:1 (1:1) | ||
| 2nd (2nd leg) | Zalgiris Kaunas | - | Rangers FC | 0:0 (0:0) | ||
| 1st(1st leg): 26/07/2000 19:45 | 2nd (2nd leg): 02/08/2000 15:30 | Winner: Rangers FC | ||||
| 1st(1st leg) | Shelbourne FC | - | Rosenborg BK | 1:3 (0:2) | ||
| 2nd (2nd leg) | Rosenborg BK | - | Shelbourne FC | 1:1 (0:0) | ||
| 1st(1st leg): 26/07/2000 20:00 | 2nd (2nd leg): 02/08/2000 19:45 | Winner: Rosenborg BK | ||||
