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| 16/08/2016 | 16:00 | FK Sateska Volino | - | Metalurg Skopje | 0:3 | |
| 17/08/2016 | 16:00 | FK Čaklani | - | FK Rabotnički | 1:6 | |
| 16:00 | FK Vlaznimi | - | FK Teteks | 0:1 | ||
| 16:00 | FK Fortuna | - | FK Pobeda Junior | 0:3 | ||
| 16:00 | FK Belasica | - | FK Pelister | 1:3 pso | ||
| 16:00 | Akademija Pandev | - | Makedonija GP | 5:0 | ||
| 16:00 | FK Ljuboten | - | FK Turnovo | 0:6 | ||
| 16:00 | Vardar Negotino | - | KF Shkupi | 0:2 | ||
| 16:00 | FK Gorno Lisiče | - | FK Renova | 1:3 | ||
| 16:00 | FK Novaci 2005 | - | FK Skopje | 2:1 | ||
| 16:00 | FK Maleš Berovo | - | Sileks Kratovo | 0:1 | ||
| 16:00 | FK Miravci | - | FK Vlazrimi 77 | 0:3 | ||
| 24/08/2016 | 15:30 | Skënderbeu Poroj | - | Vardar Skopje | 0:9 | |
| 31/08/2016 | 15:00 | Golemo Konjari | - | KF Shkëndija 79 | 0:11 |
