| 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 |  |
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| 4. Ronde | 23.08.2023 | KF Gostivari | - | FK Rabotnički | 2:0 | ||||
| 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 | ||||
| 12. Ronde | 29.10.2023 | KF Shkupi | - | FK Rabotnički | 3:0 | ||||
| 13. Ronde | 04.11.2023 | FK Rabotnički | - | Sileks Kratovo | 1:0 | ||||
| 15. Ronde | 26.11.2023 | FK Rabotnički | - | KF Gostivari | 0:0 | ||||
| 16. Ronde | 29.11.2023 | KF Shkëndija 79 | - | FK Rabotnički | 2:0 | ||||
| 18. Ronde | 10.12.2023 | FK Voska Sport | - | FK Rabotnički | 3:2 |  |
Noord-Macedonië