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