| 1. Round | 25/07/2009 | NK Osijek | - | Hajduk Split | 1:1 | ||||
| 2. Round | 01/08/2009 | HNK Šibenik | - | NK Osijek | 2:2 | ||||
| 3. Round | 08/08/2009 | NK Osijek | - | NK Karlovac | 0:1 | ||||
| 4. Round | 16/08/2009 | Dinamo Zagreb | - | NK Osijek | 5:0 |  |
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| 5. Round | 22/08/2009 | NK Osijek | - | NK Međimurje | 3:1 | |
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| 16. Round | 28/11/2009 | Hajduk Split | - | NK Osijek | 1:0 | ||||
| 17. Round | 05/12/2009 | NK Osijek | - | HNK Šibenik | 3:0 | ||||
| 19. Round | 06/03/2010 | NK Osijek | - | Dinamo Zagreb | 0:1 | ||||
| 22. Round | 27/03/2010 | NK Istra 1961 | - | NK Osijek | 1:3 | ||||
| 25. Round | 14/04/2010 | NK Inter Zaprešić | - | NK Osijek | 0:3 | ||||
| 29. Round | 08/05/2010 | NK Zagreb | - | NK Osijek | 1:0 | ||||
| 30. Round | 13/05/2010 | NK Osijek | - | HNK Cibalia | 2:0 |
Croatia