4. Round | 27/08/2016 | Sileks Kratovo | - | Makedonija GP | 1:1 | ||||
5. Round | 10/09/2016 | FK Rabotnički | - | Sileks Kratovo | 3:1 | ||||
6. Round | 18/09/2016 | Sileks Kratovo | - | FK Renova | 0:0 | ||||
8. Round | 28/09/2016 | KF Shkupi | - | Sileks Kratovo | 1:1 | ||||
9. Round | 02/10/2016 | Sileks Kratovo | - | Vardar Skopje | 1:3 | ||||
10. Round | 16/10/2016 | Sileks Kratovo | - | KF Shkëndija 79 | 1:3 | ||||
16. Round | 27/11/2016 | Sileks Kratovo | - | FK Pelister | 0:0 | ||||
18. Round | 04/12/2016 | Vardar Skopje | - | Sileks Kratovo | 1:1 |