| 2. Ronde | 13.08.2023 | Sileks Kratovo | - | FK Rabotnički | 2:0 | ||||
| 3. Ronde | 20.08.2023 | FK Rabotnički | - | Makedonija GP | 1:0 |  |
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| 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 | |
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| 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 | ||||
| 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 | ||||
| 22. Ronde | 06.03.2024 | Vardar Skopje | - | FK Rabotnički | 1:0 | ||||
| 31. Ronde | 04.05.2024 | FK Rabotnički | - | GFK Tikvesh | 3:1 | ||||
| 33. Ronde | 18.05.2024 | FK Rabotnički | - | KF Shkëndija 79 | 0:2 |
Noord-Macedonië