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| H | Shirak FC | - | BATE Borisov | 1:1 (1:1) | ||
| R | BATE Borisov | - | Shirak FC | 2:1 (1:0) | ||
| H: 12.07.2000 15:00 | R: 19.07.2000 17:30 | Sieger: BATE Borisov | ||||
| H | Skonto FC | - | Shamkir FK | 2:1 (0:0) | ||
| R | Shamkir FK | - | Skonto FC | 4:1 (1:1, 2:1) n.V. | ||
| H: 12.07.2000 17:00 | R: 19.07.2000 15:30 | Sieger: Shamkir FK | ||||
| H | KF Tiranë | - | FC Zimbru | 2:3 (2:2) | ||
| R | FC Zimbru | - | KF Tiranë | 3:2 (2:2) | ||
| H: 12.07.2000 17:30 | R: 19.07.2000 17:00 | Sieger: FC Zimbru | ||||
| H | Zalgiris Kaunas | - | NK Brotnjo | 4:0 (3:0) | ||
| R | NK Brotnjo | - | Zalgiris Kaunas | 3:0 (3:0) | ||
| H: 12.07.2000 18:30 | R: 19.07.2000 17:30 | Sieger: Zalgiris Kaunas | ||||
| H | Haka Valkeakoski | - | Linfield FC | 1:0 (0:0) | ||
| R | Linfield FC | - | Haka Valkeakoski | 2:1 (1:0) | ||
| H: 12.07.2000 19:00 | R: 19.07.2000 20:45 | Sieger: Haka Valkeakoski | ||||
| H | KÍ Klaksvík | - | Crvena Zvezda | 0:3 (0:1) | ||
| R | Crvena Zvezda | - | KÍ Klaksvík | 2:0 (2:0) | ||
| H: 12.07.2000 19:00 | R: 19.07.2000 20:00 | Sieger: Crvena Zvezda | ||||
| H | Birkirkara FC | - | KR Reykjavík | 1:2 (1:0) | ||
| R | KR Reykjavík | - | Birkirkara FC | 4:1 (2:0) | ||
| H: 12.07.2000 19:30 | R: 19.07.2000 22:00 | Sieger: KR Reykjavík | ||||
| H | F91 Dudelange | - | Levski Sofia | 0:4 (0:2) | ||
| R | Levski Sofia | - | F91 Dudelange | 2:0 (1:0) | ||
| H: 12.07.2000 20:00 | R: 19.07.2000 20:00 | Sieger: Levski Sofia | ||||
| H | FK Sloga Jugomagnat | - | Shelbourne FC | 0:1 (0:0) | ||
| R | Shelbourne FC | - | FK Sloga Jugomagnat | 1:1 (1:0) | ||
| H: 12.07.2000 20:00 | R: 19.07.2000 20:45 | Sieger: Shelbourne FC | ||||
| H | TNS Llansantffraid | - | Levadia Maardu | 2:2 (0:0) | ||
| R | Levadia Maardu | - | TNS Llansantffraid | 4:0 (1:0) | ||
| H: 12.07.2000 20:30 | R: 19.07.2000 17:00 | Sieger: Levadia Maardu | ||||
