| 5. Ronde | 27.08.2023 | FK Rabotnički | - | KF Shkëndija 79 | 1:2 | ||||
| 9. Ronde | 01.10.2023 | FK Rabotnički | - | GFK Tikvesh | 1:0 | ||||
| 10. Ronde | 07.10.2023 | FK Bregalnica Štip | - | FK Rabotnički | 2:1 | ||||
| 13. Ronde | 04.11.2023 | FK Rabotnički | - | Sileks Kratovo | 1:0 | ||||
| 14. Ronde | 12.11.2023 | Makedonija GP | - | FK Rabotnički | 0:1 | ||||
| 15. Ronde | 26.11.2023 | FK Rabotnički | - | KF Gostivari | 0:0 | ||||
| 17. Ronde | 03.12.2023 | FK Rabotnički | - | FK AP Brera Strumica | 1:0 | ||||
| 19. Ronde | 18.02.2024 | FK Rabotnički | - | FC Struga | 0:0 | ||||
| 22. Ronde | 06.03.2024 | Vardar Skopje | - | FK Rabotnički | 1:0 | ||||
| 23. Ronde | 10.03.2024 | KF Shkupi | - | FK Rabotnički | 3:2 |
Cyprus