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| H (Match allé) | FK Drina | - | Radnik Bijeljina | 0:1 | ||
| R (match retour) | Radnik Bijeljina | - | FK Drina | 0:0 | ||
| H (Match allé): 01.10.2008 15:30 | R (match retour): 08.10.2008 15:00 | vainqueur: Radnik Bijeljina | ||||
| H (Match allé) | Zvijezda Gradačac | - | Velež Mostar | 4:1 | ||
| R (match retour) | Velež Mostar | - | Zvijezda Gradačac | 3:0 | ||
| H (Match allé): 01.10.2008 15:30 | R (match retour): 08.10.2008 15:00 | vainqueur: Velež Mostar | ||||
| H (Match allé) | NK GOŠK Gabela | - | Olimpic Sarajevo | 2:1 | ||
| R (match retour) | Olimpic Sarajevo | - | NK GOŠK Gabela | 2:0 | ||
| H (Match allé): 01.10.2008 15:30 | R (match retour): 08.10.2008 15:00 | vainqueur: Olimpic Sarajevo | ||||
| H (Match allé) | NK Travnik | - | Slavija Sarajevo | 0:1 | ||
| R (match retour) | Slavija Sarajevo | - | NK Travnik | 3:1 | ||
| H (Match allé): 01.10.2008 15:30 | R (match retour): 08.10.2008 15:00 | vainqueur: Slavija Sarajevo | ||||
| H (Match allé) | Radnik Lipnica | - | HNK Orašje | 4:4 | ||
| R (match retour) | HNK Orašje | - | Radnik Lipnica | 2:0 | ||
| H (Match allé): 01.10.2008 15:30 | R (match retour): 08.10.2008 15:00 | vainqueur: HNK Orašje | ||||
| H (Match allé) | Široki Brijeg | - | FK Modriča | 3:0 | ||
| R (match retour) | FK Modriča | - | Široki Brijeg | 2:0 | ||
| H (Match allé): 01.10.2008 15:30 | R (match retour): 08.10.2008 15:00 | vainqueur: Široki Brijeg | ||||
| H (Match allé) | FK Sutjeska Foča | - | Zrinjski Mostar | 0:1 | ||
| R (match retour) | Zrinjski Mostar | - | FK Sutjeska Foča | 2:1 | ||
| H (Match allé): 01.10.2008 15:30 | R (match retour): 07.10.2008 15:00 | vainqueur: Zrinjski Mostar | ||||
| H (Match allé) | Sloboda Tuzla | - | Famos Hrasnica | 3:1 | ||
| R (match retour) | Famos Hrasnica | - | Sloboda Tuzla | 1:2 | ||
| H (Match allé): 08.10.2008 15:00 | R (match retour): 14.10.2008 15:00 | vainqueur: Sloboda Tuzla | ||||
