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 | ||||
6. Round | 31/08/2008 | NK Osijek | - | Hajduk Split | 1:2 | ||||
7. Round | 14/09/2008 | Slaven Belupo | - | NK Osijek | 4:2 | ||||
8. Round | 21/09/2008 | HNK Rijeka | - | NK Osijek | 0:0 | ||||
9. Round | 28/09/2008 | NK Osijek | - | HNK Šibenik | 1:3 | ||||
13. Round | 02/11/2008 | HNK Cibalia | - | NK Osijek | 0:3 | ||||
16. Round | 23/11/2008 | NK Osijek | - | NK Zagreb | 0:2 | ||||
18. Round | 07/12/2008 | NK Osijek | - | Slaven Belupo | 0:0 | ||||
22. Round | 15/03/2009 | NK Inter Zaprešić | - | NK Osijek | 0:1 | ||||
31. Round | 17/05/2009 | NK Osijek | - | HNK Rijeka | 1:2 | ||||
33. Round | 31/05/2009 | NK Osijek | - | Slaven Belupo | 1:2 |