| 1. Ronde | 07.08.2023 | FK Rabotnički | - | KF Shkupi | 3:1 |  |
|||
| 2. Ronde | 13.08.2023 | Sileks Kratovo | - | FK Rabotnički | 2:0 | ||||
| 3. Ronde | 20.08.2023 | FK Rabotnički | - | Makedonija GP | 1:0 | ||||
| 4. Ronde | 23.08.2023 | KF Gostivari | - | FK Rabotnički | 2:0 | ||||
| 5. Ronde | 27.08.2023 | FK Rabotnički | - | KF Shkëndija 79 | 1:2 | ||||
| 6. Ronde | 02.09.2023 | FK AP Brera Strumica | - | FK Rabotnički | 0:0 | ||||
| 7. Ronde | 17.09.2023 | FK Rabotnički | - | FK Voska Sport | 2:0 |  |
|||
| 8. Ronde | 24.09.2023 | FC Struga | - | FK Rabotnički | 1:0 | ||||
| 9. Ronde | 01.10.2023 | FK Rabotnički | - | GFK Tikvesh | 1:0 | |
|||
| 10. Ronde | 07.10.2023 | FK Bregalnica Štip | - | FK Rabotnički | 2:1 | |
|||
| 11. Ronde | 22.10.2023 | FK Rabotnički | - | Vardar Skopje | 0:1 | ||||
| 12. Ronde | 29.10.2023 | KF Shkupi | - | FK Rabotnički | 3:0 | |
|||
| 16. Ronde | 29.11.2023 | KF Shkëndija 79 | - | FK Rabotnički | 2:0 | ||||
| 19. Ronde | 18.02.2024 | FK Rabotnički | - | FC Struga | 0:0 | ||||
| 20. Ronde | 25.02.2024 | GFK Tikvesh | - | FK Rabotnički | 2:0 | |
|||
| 22. Ronde | 06.03.2024 | Vardar Skopje | - | FK Rabotnički | 1:0 |
Noord-Macedonië