| 1. Round | 06/08/2023 | GFK Tikvesh | - | Makedonija GP | 1:0 | ||||
| 2. Round | 13/08/2023 | Makedonija GP | - | FK Bregalnica Štip | 1:0 | ||||
| 3. Round | 20/08/2023 | FK Rabotnički | - | Makedonija GP | 1:0 | ||||
| 4. Round | 23/08/2023 | Makedonija GP | - | KF Shkupi | 0:0 | ||||
| 5. Round | 27/08/2023 | Sileks Kratovo | - | Makedonija GP | 2:2 | ||||
| 6. Round | 02/09/2023 | Vardar Skopje | - | Makedonija GP | 2:1 | ||||
| 7. Round | 17/09/2023 | Makedonija GP | - | KF Gostivari | 3:0 | ||||
| 8. Round | 24/09/2023 | KF Shkëndija 79 | - | Makedonija GP | 1:0 | ||||
| 10. Round | 07/10/2023 | FK Voska Sport | - | Makedonija GP | 2:1 | ||||
| 11. Round | 22/10/2023 | Makedonija GP | - | FC Struga | 0:3 | ||||
| 12. Round | 29/10/2023 | Makedonija GP | - | GFK Tikvesh | 1:1 | ||||
| 13. Round | 04/11/2023 | FK Bregalnica Štip | - | Makedonija GP | 2:3 | ||||
| 14. Round | 12/11/2023 | Makedonija GP | - | FK Rabotnički | 0:1 | ||||
| 15. Round | 26/11/2023 | KF Shkupi | - | Makedonija GP | 1:0 | ||||
| 16. Round | 29/11/2023 | Makedonija GP | - | Sileks Kratovo | 1:0 | ||||
| 17. Round | 02/12/2023 | Makedonija GP | - | Vardar Skopje | 0:1 | ||||
| 18. Round | 09/12/2023 | KF Gostivari | - | Makedonija GP | 1:0 |
North Macedonia
Albania