| 3. Round | 21/08/2023 | FC Struga | - | FK AP Brera Strumica | 1:2 | ||||
| 8. Round | 24/09/2023 | FC Struga | - | FK Rabotnički | 1:0 |  |
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| 4. Round | 27/09/2023 | FK Voska Sport | - | FC Struga | 0:1 | ||||
| 2. Round | 04/10/2023 | KF Shkëndija 79 | - | FC Struga | 1:0 | ||||
| 10. Round | 08/10/2023 | FC Struga | - | Sileks Kratovo | 2:0 | ||||
| 11. Round | 22/10/2023 | Makedonija GP | - | FC Struga | 0:3 | ||||
| 13. Round | 05/11/2023 | FC Struga | - | KF Shkëndija 79 | 2:1 | ||||
| 14. Round | 11/11/2023 | FK AP Brera Strumica | - | FC Struga | 2:1 | ||||
| 19. Round | 18/02/2024 | FK Rabotnički | - | FC Struga | 0:0 | ||||
| 20. Round | 24/02/2024 | FC Struga | - | KF Shkupi | 2:2 | ||||
| 21. Round | 03/03/2024 | Sileks Kratovo | - | FC Struga | 0:0 | ||||
| 23. Round | 10/03/2024 | FC Struga | - | FK AP Brera Strumica | 3:1 | ||||
| 25. Round | 31/03/2024 | FC Struga | - | FK Voska Sport | 3:1 | ||||
| 27. Round | 14/04/2024 | FC Struga | - | FK Bregalnica Štip | 2:2 | ||||
| 28. Round | 21/04/2024 | Makedonija GP | - | FC Struga | 0:1 | ||||
| 31. Round | 04/05/2024 | FC Struga | - | KF Gostivari | 1:0 | ||||
| 32. Round | 12/05/2024 | KF Shkëndija 79 | - | FC Struga | 0:2 | ||||
| 33. Round | 18/05/2024 | FC Struga | - | KF Shkupi | 1:2 |
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