| 1. Jornada | 25.07.2009 | NK Osijek | - | Hajduk Split | 1:1 |  |
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| 2. Jornada | 01.08.2009 | HNK Šibenik | - | NK Osijek | 2:2 | ||||
| 3. Jornada | 08.08.2009 | NK Osijek | - | NK Karlovac | 0:1 | ||||
| 4. Jornada | 16.08.2009 | Dinamo Zagreb | - | NK Osijek | 5:0 | ||||
| 6. Jornada | 29.08.2009 | NK Croatia Sesvete | - | NK Osijek | 1:2 | ||||
| 7. Jornada | 12.09.2009 | NK Osijek | - | NK Istra 1961 | 3:0 |  |
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| 8. Jornada | 19.09.2009 | NK Osijek | - | NK Zadar | 3:0 | ||||
| 9. Jornada | 26.09.2009 | Slaven Belupo | - | NK Osijek | 5:2 | |
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| 10. Jornada | 03.10.2009 | NK Osijek | - | NK Inter Zaprešić | 4:2 | ||||
| 11. Jornada | 17.10.2009 | HNK Rijeka | - | NK Osijek | 1:1 | |
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| 12. Jornada | 24.10.2009 | NK Osijek | - | Lokomotiva Zagreb | 3:0 | |
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| 14. Jornada | 07.11.2009 | NK Osijek | - | NK Zagreb | 5:3 | |
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| 15. Jornada | 21.11.2009 | HNK Cibalia | - | NK Osijek | 1:1 | |
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| 16. Jornada | 28.11.2009 | Hajduk Split | - | NK Osijek | 1:0 | ||||
| 17. Jornada | 05.12.2009 | NK Osijek | - | HNK Šibenik | 3:0 |
Croacia