| 2. Round | 13/08/2023 | FK AP Brera Strumica | - | FK Voska Sport | 2:0 |  |
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| 3. Round | 21/08/2023 | FC Struga | - | FK AP Brera Strumica | 1:2 | ||||
| 4. Round | 24/08/2023 | FK AP Brera Strumica | - | GFK Tikvesh | 2:0 | ||||
| 6. Round | 02/09/2023 | FK AP Brera Strumica | - | FK Rabotnički | 0:0 | ||||
| 7. Round | 16/09/2023 | KF Shkupi | - | FK AP Brera Strumica | 1:0 | ||||
| 8. Round | 24/09/2023 | FK AP Brera Strumica | - | Sileks Kratovo | 1:1 | ||||
| 12. Round | 29/10/2023 | Vardar Skopje | - | FK AP Brera Strumica | 1:0 | ||||
| 14. Round | 11/11/2023 | FK AP Brera Strumica | - | FC Struga | 2:1 | ||||
| 15. Round | 26/11/2023 | GFK Tikvesh | - | FK AP Brera Strumica | 1:0 | ||||
| 16. Round | 29/11/2023 | FK AP Brera Strumica | - | FK Bregalnica Štip | 1:1 | |
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| 17. Round | 03/12/2023 | FK Rabotnički | - | FK AP Brera Strumica | 1:0 | ||||
| 18. Round | 10/12/2023 | FK AP Brera Strumica | - | KF Shkupi | 0:1 | |
North Macedonia