9. Round | 01/10/2023 | Sileks Kratovo | - | FK Voska Sport | 4:2 | ||||
10. Round | 08/10/2023 | FC Struga | - | Sileks Kratovo | 2:0 | ||||
11. Round | 22/10/2023 | Sileks Kratovo | - | GFK Tikvesh | 1:0 | ||||
12. Round | 28/10/2023 | Sileks Kratovo | - | FK Bregalnica Štip | 0:0 | ||||
13. Round | 04/11/2023 | FK Rabotnički | - | Sileks Kratovo | 1:0 | ||||
14. Round | 12/11/2023 | Sileks Kratovo | - | KF Shkupi | 2:1 | ||||
16. Round | 29/11/2023 | Makedonija GP | - | Sileks Kratovo | 1:0 | ||||
17. Round | 03/12/2023 | Sileks Kratovo | - | KF Gostivari | 1:1 | ||||
15. Round | 06/12/2023 | Sileks Kratovo | - | Vardar Skopje | 3:2 | ||||
18. Round | 10/12/2023 | KF Shkëndija 79 | - | Sileks Kratovo | 3:1 | ||||
33. Round | 18/05/2024 | FK Bregalnica Štip | - | Sileks Kratovo | 1:1 |