| 1. Jornada | 27.07.2008 | NK Croatia Sesvete | - | NK Osijek | 1:1 | ||||
| 2. Jornada | 03.08.2008 | NK Osijek | - | HNK Cibalia | 2:0 | ||||
| 3. Jornada | 10.08.2008 | NK Zadar | - | NK Osijek | 2:2 | ||||
| 4. Jornada | 17.08.2008 | NK Osijek | - | NK Varteks | 2:1 | ||||
| 5. Jornada | 24.08.2008 | NK Zagreb | - | NK Osijek | 2:1 | ||||
| 6. Jornada | 31.08.2008 | NK Osijek | - | Hajduk Split | 1:2 | ||||
| 8. Jornada | 21.09.2008 | HNK Rijeka | - | NK Osijek | 0:0 | ||||
| 9. Jornada | 28.09.2008 | NK Osijek | - | HNK Šibenik | 1:3 | ||||
| 10. Jornada | 05.10.2008 | Dinamo Zagreb | - | NK Osijek | 1:0 | ||||
| 14. Jornada | 09.11.2008 | NK Osijek | - | NK Zadar | 3:0 | ||||
| 16. Jornada | 23.11.2008 | NK Osijek | - | NK Zagreb | 0:2 | ||||
| 17. Jornada | 30.11.2008 | Hajduk Split | - | NK Osijek | 3:1 | ||||
| 19. Jornada | 22.02.2009 | NK Osijek | - | HNK Rijeka | 2:2 | ||||
| 22. Jornada | 15.03.2009 | NK Inter Zaprešić | - | NK Osijek | 0:1 |
Croacia