| 1. Jornada | 19.07.2019 | NK Osijek | - | Slaven Belupo | 2:0 | ||||
| 7. Jornada | 31.08.2019 | NK Istra 1961 | - | NK Osijek | 0:0 | ||||
| 8. Jornada | 15.09.2019 | NK Osijek | - | NK Varaždin | 2:2 | ||||
| 9. Jornada | 20.09.2019 | Lokomotiva Zagreb | - | NK Osijek | 2:1 |  |
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| 16. Jornada | 24.11.2019 | NK Osijek | - | NK Istra 1961 | 1:0 | ||||
| 19. Jornada | 15.12.2019 | NK Osijek | - | Slaven Belupo | 3:2 | ||||
| 23. Jornada | 22.02.2020 | HNK Rijeka | - | NK Osijek | 1:0 | ||||
| 24. Jornada | 29.02.2020 | NK Osijek | - | Hajduk Split | 0:0 | ||||
| 26. Jornada | 07.03.2020 | NK Osijek | - | NK Varaždin | 2:0 | ||||
| 27. Jornada | 07.06.2020 | Lokomotiva Zagreb | - | NK Osijek | 0:1 | ||||
| 28. Jornada | 13.06.2020 | Slaven Belupo | - | NK Osijek | 0:0 | ||||
| 29. Jornada | 17.06.2020 | NK Osijek | - | HNK Gorica | 2:1 | |
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| 31. Jornada | 27.06.2020 | Dinamo Zagreb | - | NK Osijek | 0:0 | |
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| 36. Jornada | 25.07.2020 | NK Osijek | - | Lokomotiva Zagreb | 1:2 |
Croacia