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 | ||||
7. Round | 14/09/2008 | Slaven Belupo | - | NK Osijek | 4:2 | ||||
9. Round | 28/09/2008 | NK Osijek | - | HNK Šibenik | 1:3 | ||||
20. Round | 01/03/2009 | HNK Šibenik | - | NK Osijek | 1:1 | ||||
25. Round | 11/04/2009 | NK Zagreb | - | NK Osijek | 1:0 | ||||
26. Round | 19/04/2009 | HNK Cibalia | - | NK Osijek | 1:1 |