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 | ||||
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 |