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| H | Inter Baku | - | FK Rabotnički | 0:0 (0:0) | ||
| R | FK Rabotnički | - | Inter Baku | 1:1 (0:0) | ||
| H: 15.07.2008 18:00 | R: 22.07.2008 17:00 | Sieger: Inter Baku | ||||
| H | Tampere United | - | FK Budućnost Podgorica | 2:1 (1:0) | ||
| R | FK Budućnost Podgorica | - | Tampere United | 1:1 (0:1) | ||
| H: 15.07.2008 18:00 | R: 23.07.2008 20:00 | Sieger: Tampere United | ||||
| H | BATE Borisov | - | Valur Reykjavík | 2:0 (0:0) | ||
| R | Valur Reykjavík | - | BATE Borisov | 0:1 (0:1) | ||
| H: 15.07.2008 18:00 | R: 23.07.2008 21:15 | Sieger: BATE Borisov | ||||
| H | Anorthosis Famagusta | - | Pyunik FC | 1:0 (0:0) | ||
| R | Pyunik FC | - | Anorthosis Famagusta | 0:2 (0:1) | ||
| H: 15.07.2008 19:00 | R: 23.07.2008 15:30 | Sieger: Anorthosis Famagusta | ||||
| H | F91 Dudelange | - | NK Domžale | 0:1 (0:0) | ||
| R | NK Domžale | - | F91 Dudelange | 2:0 (0:0) | ||
| H: 15.07.2008 19:00 | R: 23.07.2008 20:45 | Sieger: NK Domžale | ||||
| H | Llanelli AFC | - | FK Ventspils | 1:0 (1:0) | ||
| R | FK Ventspils | - | Llanelli AFC | 4:0 (2:0) | ||
| H: 15.07.2008 19:35 | R: 22.07.2008 17:00 | Sieger: FK Ventspils | ||||
| H | Valletta FC | - | FC Artmedia Petržalka | 0:2 (0:0) | ||
| R | FC Artmedia Petržalka | - | Valletta FC | 1:0 (1:0) | ||
| H: 15.07.2008 20:00 | R: 23.07.2008 20:15 | Sieger: FC Artmedia Petržalka | ||||
| H | Dinamo Tiranë | - | FK Modriča | 0:2 (0:0) | ||
| R | FK Modriča | - | Dinamo Tiranë | 2:1 (0:0) | ||
| H: 15.07.2008 20:00 | R: 23.07.2008 20:00 | Sieger: FK Modriča | ||||
| H | FC Santa Coloma | - | FBK Kaunas | 1:4 (0:3) | ||
| R | FBK Kaunas | - | FC Santa Coloma | 3:1 (2:1) | ||
| H: 15.07.2008 20:30 | R: 22.07.2008 18:30 | Sieger: FBK Kaunas | ||||
| H | SS Murata | - | IFK Göteborg | 0:5 (0:3) | ||
| R | IFK Göteborg | - | SS Murata | 4:0 (1:0) | ||
| H: 15.07.2008 20:30 | R: 23.07.2008 20:00 | Sieger: IFK Göteborg | ||||
| H | Dinamo Tbilisi | - | NSÍ Runavík | 3:0 (3:0) | ||
| R | NSÍ Runavík | - | Dinamo Tbilisi | 1:0 (1:0) | ||
| H: 16.07.2008 16:00 | R: 22.07.2008 20:00 | Sieger: Dinamo Tbilisi | ||||
| H | FK Aktobe | - | FC Sheriff | 1:0 (0:0) | ||
| R | FC Sheriff | - | FK Aktobe | 4:0 (0:0) | ||
| H: 16.07.2008 17:00 | R: 22.07.2008 19:00 | Sieger: FC Sheriff | ||||
| H | Linfield FC | - | Dinamo Zagreb | 0:2 (0:1) | ||
| R | Dinamo Zagreb | - | Linfield FC | 1:1 (1:0) | ||
| H: 16.07.2008 20:45 | R: 23.07.2008 20:45 | Sieger: Dinamo Zagreb | ||||
| H | Drogheda United | - | FC Levadia | 2:1 (0:1) | ||
| R | FC Levadia | - | Drogheda United | 0:1 (0:0) | ||
| H: 16.07.2008 20:45 | R: 23.07.2008 17:30 | Sieger: Drogheda United | ||||
