| 2. Round | 30/07/2023 | NK Rudeš | - | NK Osijek | 3:4 | ||||
| 4. Round | 13/08/2023 | NK Istra 1961 | - | NK Osijek | 4:4 |  |
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| 5. Round | 20/08/2023 | NK Osijek | - | HNK Gorica | 1:0 | ||||
| 10. Round | 30/09/2023 | Slaven Belupo | - | NK Osijek | 1:0 | |
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| 13. Round | 28/10/2023 | NK Osijek | - | NK Istra 1961 | 3:1 | ||||
| 14. Round | 04/11/2023 | HNK Gorica | - | NK Osijek | 3:0 |
Bosnia-Herzegovina