| 4. Round | 23/08/2023 | KF Gostivari | - | FK Rabotnički | 2:0 | ||||
| 15. Round | 26/11/2023 | FK Rabotnički | - | KF Gostivari | 0:0 | ||||
| 17. Round | 03/12/2023 | FK Rabotnički | - | FK AP Brera Strumica | 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 | ||||
| 22. Round | 06/03/2024 | Vardar Skopje | - | FK Rabotnički | 1:0 |  |
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| 23. Round | 10/03/2024 | KF Shkupi | - | FK Rabotnički | 3:2 | ||||
| 24. Round | 17/03/2024 | FK Rabotnički | - | FC Struga | 1:2 | ||||
| 25. Round | 31/03/2024 | FK AP Brera Strumica | - | FK Rabotnički | 2:1 | ||||
| 26. Round | 07/04/2024 | FK Voska Sport | - | FK Rabotnički | 1:1 | ||||
| 28. Round | 20/04/2024 | FK Bregalnica Štip | - | FK Rabotnički | 0:1 | ||||
| 29. Round | 28/04/2024 | FK Rabotnički | - | Makedonija GP | 1:1 | ||||
| 30. Round | 01/05/2024 | Sileks Kratovo | - | FK Rabotnički | 0:1 | ||||
| 31. Round | 04/05/2024 | FK Rabotnički | - | GFK Tikvesh | 3:1 |
North Macedonia