| 1. Jornada | 27.07.2008 | NK Croatia Sesvete | - | NK Osijek | 1:1 | ||||
| 2. Jornada | 03.08.2008 | NK Osijek | - | HNK Cibalia | 2:0 |  |
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| 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 | ||||
| 7. Jornada | 14.09.2008 | Slaven Belupo | - | NK Osijek | 4:2 | ||||
| 9. Jornada | 28.09.2008 | NK Osijek | - | HNK Šibenik | 1:3 | ||||
| 20. Jornada | 01.03.2009 | HNK Šibenik | - | NK Osijek | 1:1 | ||||
| 25. Jornada | 11.04.2009 | NK Zagreb | - | NK Osijek | 1:0 | ||||
| 26. Jornada | 19.04.2009 | HNK Cibalia | - | NK Osijek | 1:1 |
Croacia