| 1. Jornada | 27.07.2008 | NK Croatia Sesvete | - | NK Osijek | 1:1 | ||||
| 2. Jornada | 03.08.2008 | NK Osijek | - | HNK Cibalia | 2:0 | ||||
| 3. Jornada | 10.08.2008 | NK Zadar | - | NK Osijek | 2:2 |  |
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| 4. Jornada | 17.08.2008 | NK Osijek | - | NK Varteks | 2:1 | ||||
| 5. Jornada | 24.08.2008 | NK Zagreb | - | NK Osijek | 2:1 | |
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| 6. Jornada | 31.08.2008 | NK Osijek | - | Hajduk Split | 1:2 | ||||
| 7. Jornada | 14.09.2008 | Slaven Belupo | - | NK Osijek | 4:2 | |
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| 23. Jornada | 22.03.2009 | Dinamo Zagreb | - | NK Osijek | 0:0 | ||||
| 25. Jornada | 11.04.2009 | NK Zagreb | - | NK Osijek | 1:0 | ||||
| 33. Jornada | 31.05.2009 | NK Osijek | - | Slaven Belupo | 1:2 |
Croacia