1. Round | 27/07/2008 | NK Croatia Sesvete | - | NK Osijek | 1:1 | ||||
2. Round | 03/08/2008 | NK Osijek | - | HNK Cibalia | 2:0 | ||||
3. Round | 10/08/2008 | NK Zadar | - | NK Osijek | 2:2 | ||||
4. Round | 17/08/2008 | NK Osijek | - | NK Varteks | 2:1 | ||||
5. Round | 24/08/2008 | NK Zagreb | - | NK Osijek | 2:1 | ||||
6. Round | 31/08/2008 | NK Osijek | - | Hajduk Split | 1:2 | ||||
8. Round | 21/09/2008 | HNK Rijeka | - | NK Osijek | 0:0 | ||||
9. Round | 28/09/2008 | NK Osijek | - | HNK Šibenik | 1:3 | ||||
10. Round | 05/10/2008 | Dinamo Zagreb | - | NK Osijek | 1:0 | ||||
14. Round | 09/11/2008 | NK Osijek | - | NK Zadar | 3:0 | ||||
16. Round | 23/11/2008 | NK Osijek | - | NK Zagreb | 0:2 | ||||
17. Round | 30/11/2008 | Hajduk Split | - | NK Osijek | 3:1 | ||||
19. Round | 22/02/2009 | NK Osijek | - | HNK Rijeka | 2:2 | ||||
22. Round | 15/03/2009 | NK Inter Zaprešić | - | NK Osijek | 0:1 |