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