| 5. Round | 19/08/2023 | NK Aluminij | - | Olimpija Ljubljana | 4:5 |  |
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| 6. Round | 27/08/2023 | Olimpija Ljubljana | - | NK Celje | 2:4 | ||||
| 7. Round | 03/09/2023 | NŠ Mura | - | Olimpija Ljubljana | 1:3 | |
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| 8. Round | 16/09/2023 | Olimpija Ljubljana | - | NK Maribor | 2:1 | ||||
| 9. Round | 23/09/2023 | NK Bravo | - | Olimpija Ljubljana | 4:2 | |
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| 10. Round | 28/09/2023 | Olimpija Ljubljana | - | FC Koper | 1:1 | ||||
| 11. Round | 01/10/2023 | NK Rogaška | - | Olimpija Ljubljana | 0:2 | ||||
| 12. Round | 08/10/2023 | Olimpija Ljubljana | - | NK Radomlje | 1:1 | ||||
| 13. Round | 21/10/2023 | NK Domžale | - | Olimpija Ljubljana | 0:2 | ||||
| 14. Round | 29/10/2023 | Olimpija Ljubljana | - | NK Aluminij | 0:0 | ||||
| 16. Round | 12/11/2023 | Olimpija Ljubljana | - | NŠ Mura | 1:0 | ||||
| 3. Round | 25/11/2023 | NK Radomlje | - | Olimpija Ljubljana | 0:2 | ||||
| 17. Round | 03/12/2023 | NK Maribor | - | Olimpija Ljubljana | 3:1 | |
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| 19. Round | 10/12/2023 | FC Koper | - | Olimpija Ljubljana | 2:4 |
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