| 7. Round | 17/09/2023 | FK Rabotnički | - | FK Voska Sport | 2:0 | ||||
| 8. Round | 24/09/2023 | FC Struga | - | FK Rabotnički | 1:0 | ||||
| 19. Round | 18/02/2024 | FK Rabotnički | - | FC Struga | 0:0 | ||||
| 20. Round | 25/02/2024 | GFK Tikvesh | - | FK Rabotnički | 2:0 | ||||
| 21. Round | 03/03/2024 | FK Rabotnički | - | FK Bregalnica Štip | 2:0 |  |
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| 24. Round | 17/03/2024 | FK Rabotnički | - | FC Struga | 1:2 | |
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| 26. Round | 07/04/2024 | FK Voska Sport | - | FK Rabotnički | 1:1 | ||||
| 28. Round | 20/04/2024 | FK Bregalnica Štip | - | FK Rabotnički | 0:1 | ||||
| 31. Round | 04/05/2024 | FK Rabotnički | - | GFK Tikvesh | 3:1 | ||||
| 32. Round | 12/05/2024 | KF Gostivari | - | FK Rabotnički | 0:0 | ||||
| 33. Round | 18/05/2024 | FK Rabotnički | - | KF Shkëndija 79 | 0:2 |
North Macedonia