| 10. Round | 05/10/2008 | Dinamo Zagreb | - | NK Osijek | 1:0 | ||||
| 11. Round | 19/10/2008 | NK Osijek | - | NK Inter Zaprešić | 2:1 | ||||
| 12. Round | 26/10/2008 | NK Osijek | - | NK Croatia Sesvete | 4:2 |  |
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| 13. Round | 02/11/2008 | HNK Cibalia | - | NK Osijek | 0:3 | ||||
| 14. Round | 09/11/2008 | NK Osijek | - | NK Zadar | 3:0 | ||||
| 15. Round | 16/11/2008 | NK Varteks | - | NK Osijek | 0:0 | ||||
| 16. Round | 23/11/2008 | NK Osijek | - | NK Zagreb | 0:2 | ||||
| 17. Round | 30/11/2008 | Hajduk Split | - | NK Osijek | 3:1 | ||||
| 18. Round | 07/12/2008 | NK Osijek | - | Slaven Belupo | 0:0 | ||||
| 19. Round | 22/02/2009 | NK Osijek | - | HNK Rijeka | 2:2 | ||||
| 22. Round | 15/03/2009 | NK Inter Zaprešić | - | NK Osijek | 0:1 | ||||
| 23. Round | 22/03/2009 | Dinamo Zagreb | - | NK Osijek | 0:0 | ||||
| 24. Round | 05/04/2009 | NK Osijek | - | Hajduk Split | 1:0 | ||||
| 26. Round | 19/04/2009 | HNK Cibalia | - | NK Osijek | 1:1 | ||||
| 27. Round | 22/04/2009 | NK Osijek | - | NK Inter Zaprešić | 1:1 | ||||
| 28. Round | 26/04/2009 | NK Croatia Sesvete | - | NK Osijek | 1:1 | ||||
| 29. Round | 03/05/2009 | NK Osijek | - | NK Zadar | 1:0 | ||||
| 32. Round | 24/05/2009 | HNK Šibenik | - | NK Osijek | 2:1 |  |
Brazil