| 8. Round | 24/09/2023 | FC Struga | - | FK Rabotnički | 1:0 | ||||
| 9. Round | 01/10/2023 | FK Rabotnički | - | GFK Tikvesh | 1:0 | ||||
| 10. Round | 07/10/2023 | FK Bregalnica Štip | - | FK Rabotnički | 2:1 | ||||
| 11. Round | 22/10/2023 | FK Rabotnički | - | Vardar Skopje | 0:1 |  |
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| 15. Round | 26/11/2023 | FK Rabotnički | - | KF Gostivari | 0:0 | ||||
| 16. Round | 29/11/2023 | KF Shkëndija 79 | - | FK Rabotnički | 2:0 | ||||
| 17. Round | 03/12/2023 | FK Rabotnički | - | FK AP Brera Strumica | 1:0 |  |
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| 18. Round | 10/12/2023 | FK Voska Sport | - | FK Rabotnički | 3:2 | |
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| 21. Round | 03/03/2024 | FK Rabotnički | - | FK Bregalnica Štip | 2:0 | |
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| 23. Round | 10/03/2024 | KF Shkupi | - | FK Rabotnički | 3:2 | |
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| 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 | ||||
| 27. Round | 14/04/2024 | FK Rabotnički | - | Vardar Skopje | 2:0 | ||||
| 28. Round | 20/04/2024 | FK Bregalnica Štip | - | FK Rabotnički | 0:1 |
North Macedonia