1. Round | 07/08/2016 | FK Pobeda Junior | - | FK Pelister | 0:2 | ||||
3. Round | 21/08/2016 | FK Pobeda Junior | - | Vardar Skopje | 0:1 | ||||
4. Round | 28/08/2016 | KF Shkëndija 79 | - | FK Pobeda Junior | 3:1 | ||||
7. Round | 25/09/2016 | Makedonija GP | - | FK Pobeda Junior | 1:1 | ||||
8. Round | 28/09/2016 | FK Pobeda Junior | - | FK Rabotnički | 2:1 | ||||
11. Round | 23/10/2016 | FK Pobeda Junior | - | Sileks Kratovo | 1:1 |