| 1. Round | 22/07/2023 | FC Koper | - | Olimpija Ljubljana | 2:1 | ||||
| 2. Round | 29/07/2023 | Olimpija Ljubljana | - | NK Rogaška | 5:0 |  |
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| 4. Round | 12/08/2023 | Olimpija Ljubljana | - | NK Domžale | 2:1 | ||||
| 5. Round | 19/08/2023 | NK Aluminij | - | Olimpija Ljubljana | 4:5 | ||||
| 6. Round | 27/08/2023 | Olimpija Ljubljana | - | NK Celje | 2:4 | ||||
| 9. Round | 23/09/2023 | NK Bravo | - | Olimpija Ljubljana | 4:2 |  |
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| 12. Round | 08/10/2023 | Olimpija Ljubljana | - | NK Radomlje | 1:1 | ||||
| 15. Round | 05/11/2023 | NK Celje | - | Olimpija Ljubljana | 0:1 | ||||
| 18. Round | 07/12/2023 | Olimpija Ljubljana | - | NK Bravo | 1:1 | ||||
| 23. Round | 24/02/2024 | NK Aluminij | - | Olimpija Ljubljana | 0:4 | ||||
| 27. Round | 16/03/2024 | NK Bravo | - | Olimpija Ljubljana | 1:1 | ||||
| 29. Round | 06/04/2024 | NK Rogaška | - | Olimpija Ljubljana | 2:3 | ||||
| 26. Round | 17/04/2024 | Olimpija Ljubljana | - | NK Maribor | 1:2 | ||||
| 36. Round | 19/05/2024 | Olimpija Ljubljana | - | NK Bravo | 0:1 |
Austria