| 1. Jornada | 22.07.2023 | NK Osijek | - | Slaven Belupo | 6:1 | ||||
| 2. Jornada | 30.07.2023 | NK Rudeš | - | NK Osijek | 3:4 |  |
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| 4. Jornada | 13.08.2023 | NK Istra 1961 | - | NK Osijek | 4:4 | |
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| 8. Jornada | 16.09.2023 | HNK Rijeka | - | NK Osijek | 2:1 | ||||
| 9. Jornada | 22.09.2023 | NK Osijek | - | NK Varaždin | 1:1 | ||||
| 10. Jornada | 30.09.2023 | Slaven Belupo | - | NK Osijek | 1:0 | ||||
| 11. Jornada | 07.10.2023 | NK Osijek | - | NK Rudeš | 3:0 |  |
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| 12. Jornada | 22.10.2023 | Hajduk Split | - | NK Osijek | 0:2 | ||||
| 13. Jornada | 28.10.2023 | NK Osijek | - | NK Istra 1961 | 3:1 | ||||
| 15. Jornada | 11.11.2023 | NK Osijek | - | Lokomotiva Zagreb | 1:1 | |
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| 17. Jornada | 02.12.2023 | NK Osijek | - | HNK Rijeka | 0:0 |
Croacia