| 1. Round | 19/07/2019 | NK Osijek | - | Slaven Belupo | 2:0 | ||||
| 7. Round | 31/08/2019 | NK Istra 1961 | - | NK Osijek | 0:0 | ||||
| 8. Round | 15/09/2019 | NK Osijek | - | NK Varaždin | 2:2 | ||||
| 9. Round | 20/09/2019 | Lokomotiva Zagreb | - | NK Osijek | 2:1 |  |
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| 16. Round | 24/11/2019 | NK Osijek | - | NK Istra 1961 | 1:0 | ||||
| 19. Round | 15/12/2019 | NK Osijek | - | Slaven Belupo | 3:2 | ||||
| 23. Round | 22/02/2020 | HNK Rijeka | - | NK Osijek | 1:0 | ||||
| 24. Round | 29/02/2020 | NK Osijek | - | Hajduk Split | 0:0 | ||||
| 26. Round | 07/03/2020 | NK Osijek | - | NK Varaždin | 2:0 | ||||
| 27. Round | 07/06/2020 | Lokomotiva Zagreb | - | NK Osijek | 0:1 | ||||
| 28. Round | 13/06/2020 | Slaven Belupo | - | NK Osijek | 0:0 | ||||
| 29. Round | 17/06/2020 | NK Osijek | - | HNK Gorica | 2:1 | |
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| 31. Round | 27/06/2020 | Dinamo Zagreb | - | NK Osijek | 0:0 | |
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| 36. Round | 25/07/2020 | NK Osijek | - | Lokomotiva Zagreb | 1:2 |
Croatia