| 1. Journée | 19.07.2019 | NK Osijek | - | Slaven Belupo | 2:0 | ||||
| 3. Journée | 04.08.2019 | NK Osijek | - | NK Inter Zaprešić | 3:1 | ||||
| 4. Journée | 09.08.2019 | NK Osijek | - | Dinamo Zagreb | 0:0 |  |
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| 5. Journée | 18.08.2019 | HNK Rijeka | - | NK Osijek | 1:1 | ||||
| 6. Journée | 25.08.2019 | NK Osijek | - | Hajduk Split | 1:0 | ||||
| 7. Journée | 31.08.2019 | NK Istra 1961 | - | NK Osijek | 0:0 | ||||
| 8. Journée | 15.09.2019 | NK Osijek | - | NK Varaždin | 2:2 | ||||
| 9. Journée | 20.09.2019 | Lokomotiva Zagreb | - | NK Osijek | 2:1 | ||||
| 10. Journée | 28.09.2019 | Slaven Belupo | - | NK Osijek | 0:4 | |
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| 11. Journée | 05.10.2019 | NK Osijek | - | HNK Gorica | 2:1 | |
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| 13. Journée | 27.10.2019 | Dinamo Zagreb | - | NK Osijek | 1:0 | ||||
| 14. Journée | 03.11.2019 | NK Osijek | - | HNK Rijeka | 3:2 | ||||
| 15. Journée | 10.11.2019 | Hajduk Split | - | NK Osijek | 3:2 | ||||
| 17. Journée | 30.11.2019 | NK Varaždin | - | NK Osijek | 1:1 | ||||
| 18. Journée | 08.12.2019 | NK Osijek | - | Lokomotiva Zagreb | 4:0 | ||||
| 19. Journée | 15.12.2019 | NK Osijek | - | Slaven Belupo | 3:2 |
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