| 1. Round | 06/08/2023 | FK AP Brera Strumica | - | Vardar Skopje | 1:0 | ||||
| 2. Round | 13/08/2023 | FK AP Brera Strumica | - | FK Voska Sport | 2:0 | ||||
| 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 | ||||
| 5. Round | 27/08/2023 | FK Bregalnica Štip | - | FK AP Brera Strumica | 1:0 | ||||
| 6. Round | 02/09/2023 | FK AP Brera Strumica | - | FK Rabotnički | 0:0 |  |
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| 7. Round | 16/09/2023 | KF Shkupi | - | FK AP Brera Strumica | 1:0 | ||||
| 9. Round | 30/09/2023 | Makedonija GP | - | FK AP Brera Strumica | 1:0 | ||||
| 11. Round | 22/10/2023 | KF Shkëndija 79 | - | FK AP Brera Strumica | 1:1 | |
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| 12. Round | 29/10/2023 | Vardar Skopje | - | FK AP Brera Strumica | 1:0 | ||||
| 13. Round | 04/11/2023 | FK Voska Sport | - | FK AP Brera Strumica | 1:1 | ||||
| 15. Round | 26/11/2023 | GFK Tikvesh | - | FK AP Brera Strumica | 1:0 | ||||
| 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 |
Senegal