1. Round | 06/08/2023 | FK Bregalnica Štip | - | Sileks Kratovo | 2:1 | ||||
2. Round | 13/08/2023 | Sileks Kratovo | - | FK Rabotnički | 2:0 | ||||
3. Round | 20/08/2023 | KF Shkupi | - | Sileks Kratovo | 1:1 | ||||
4. Round | 23/08/2023 | Vardar Skopje | - | Sileks Kratovo | 2:2 | ||||
7. Round | 17/09/2023 | Sileks Kratovo | - | KF Shkëndija 79 | 2:1 | ||||
10. Round | 08/10/2023 | FC Struga | - | Sileks Kratovo | 2:0 | ||||
11. Round | 22/10/2023 | Sileks Kratovo | - | GFK Tikvesh | 1:0 |