| 1. Ronde | 22.07.2023 | NK Osijek | - | Slaven Belupo | 6:1 |  |
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| 2. Ronde | 30.07.2023 | NK Rudeš | - | NK Osijek | 3:4 | |
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| 4. Ronde | 13.08.2023 | NK Istra 1961 | - | NK Osijek | 4:4 | |
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| 5. Ronde | 20.08.2023 | NK Osijek | - | HNK Gorica | 1:0 | |
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| 6. Ronde | 26.08.2023 | Lokomotiva Zagreb | - | NK Osijek | 2:2 | |
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| 7. Ronde | 03.09.2023 | NK Osijek | - | Dinamo Zagreb | 2:3 | |
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| 9. Ronde | 22.09.2023 | NK Osijek | - | NK Varaždin | 1:1 | ||||
| 10. Ronde | 30.09.2023 | Slaven Belupo | - | NK Osijek | 1:0 | ||||
| 11. Ronde | 07.10.2023 | NK Osijek | - | NK Rudeš | 3:0 | ||||
| 12. Ronde | 22.10.2023 | Hajduk Split | - | NK Osijek | 0:2 | ||||
| 13. Ronde | 28.10.2023 | NK Osijek | - | NK Istra 1961 | 3:1 | ||||
| 3. Ronde | 08.11.2023 | NK Osijek | - | Hajduk Split | 0:1 | ||||
| 15. Ronde | 11.11.2023 | NK Osijek | - | Lokomotiva Zagreb | 1:1 | ||||
| 16. Ronde | 25.11.2023 | Dinamo Zagreb | - | NK Osijek | 2:1 |
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