| 1. Round | 07/08/2023 | FK Rabotnički | - | KF Shkupi | 3:1 |  |
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| 2. Round | 13/08/2023 | Sileks Kratovo | - | FK Rabotnički | 2:0 | ||||
| 3. Round | 20/08/2023 | FK Rabotnički | - | Makedonija GP | 1:0 | ||||
| 4. Round | 23/08/2023 | KF Gostivari | - | FK Rabotnički | 2:0 | ||||
| 5. Round | 27/08/2023 | FK Rabotnički | - | KF Shkëndija 79 | 1:2 | ||||
| 6. Round | 02/09/2023 | FK AP Brera Strumica | - | FK Rabotnički | 0:0 | ||||
| 7. Round | 17/09/2023 | FK Rabotnički | - | FK Voska Sport | 2:0 |  |
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| 8. Round | 24/09/2023 | FC Struga | - | FK Rabotnički | 1:0 | ||||
| 9. Round | 01/10/2023 | FK Rabotnički | - | GFK Tikvesh | 1:0 | |
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| 10. Round | 07/10/2023 | FK Bregalnica Štip | - | FK Rabotnički | 2:1 | |
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| 11. Round | 22/10/2023 | FK Rabotnički | - | Vardar Skopje | 0:1 | ||||
| 12. Round | 29/10/2023 | KF Shkupi | - | FK Rabotnički | 3:0 | |
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| 16. Round | 29/11/2023 | KF Shkëndija 79 | - | FK Rabotnički | 2:0 | ||||
| 19. Round | 18/02/2024 | FK Rabotnički | - | FC Struga | 0:0 | ||||
| 20. Round | 25/02/2024 | GFK Tikvesh | - | FK Rabotnički | 2:0 | |
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| 22. Round | 06/03/2024 | Vardar Skopje | - | FK Rabotnički | 1:0 |
North Macedonia