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 | ||||
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 |