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 | ||||
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 |