| 12. Jornada | 26.10.2008 | NK Osijek | - | NK Croatia Sesvete | 4:2 | ||||
| 16. Jornada | 23.11.2008 | NK Osijek | - | NK Zagreb | 0:2 | ||||
| 17. Jornada | 30.11.2008 | Hajduk Split | - | NK Osijek | 3:1 | ||||
| 18. Jornada | 07.12.2008 | NK Osijek | - | Slaven Belupo | 0:0 | ||||
| 24. Jornada | 05.04.2009 | NK Osijek | - | Hajduk Split | 1:0 | ||||
| 27. Jornada | 22.04.2009 | NK Osijek | - | NK Inter Zaprešić | 1:1 |  |
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| 28. Jornada | 26.04.2009 | NK Croatia Sesvete | - | NK Osijek | 1:1 | ||||
| 29. Jornada | 03.05.2009 | NK Osijek | - | NK Zadar | 1:0 | ||||
| 33. Jornada | 31.05.2009 | NK Osijek | - | Slaven Belupo | 1:2 | |
Croacia