1. Round
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
Round of 16
21/09/2016 Metalurg Skopje - Mladost Carev Dvor dnp
14:30 Akademija Pandev - KF Shkupi 0:1 (0:0)
14:30 FK Pelister - FK Renova 2:0 (2:0)
14:30 FK Vlazrimi 77 - Vardar Skopje 1:3 (1:0)
14:30 Sileks Kratovo - FK Turnovo 2:1 (1:0)
14:30 FK Bregalnica Štip - FK Teteks 4:0 (2:0)
14:30 FK Novaci 2005 - FK Pobeda Junior 1:2 (0:0)
14:30 FK Rabotnički - KF Shkëndija 79 0:2 (0:0)
12/10/2016 Mladost Carev Dvor - Metalurg Skopje dnp
13:30 KF Shkupi - Akademija Pandev 3:1
13:30 FK Turnovo - Sileks Kratovo 3:3 (2:2)
13:30 FK Teteks - FK Bregalnica Štip 1:2 (0:0)
13:30 FK Pobeda Junior - FK Novaci 2005 5:0
19/10/2016 13:30 FK Renova - FK Pelister 3:1 (3:0)
13:30 Vardar Skopje - FK Vlazrimi 77 2:0 (1:0)
13:30 KF Shkëndija 79 - FK Rabotnički 0:0 (0:0)
Quarter-finals
23/11/2016 12:30 FK Pelister - Sileks Kratovo 1:0 (0:0)
12:30 Metalurg Skopje - Vardar Skopje 1:4 (0:4)
12:30 KF Shkupi - KF Shkëndija 79 0:0 (0:0)
12:30 FK Pobeda Junior - FK Bregalnica Štip 2:2 (1:1)
07/12/2016 12:00 Sileks Kratovo - FK Pelister 1:2 (0:1)
12:00 Vardar Skopje - Metalurg Skopje 4:1 (1:0)
12:00 KF Shkëndija 79 - KF Shkupi 4:0 (3:0)
12:00 FK Bregalnica Štip - FK Pobeda Junior 3:0 (1:0)
Semi-finals
01/03/2017 13:00 Vardar Skopje - KF Shkëndija 79 1:3 (0:2)
16:00 FK Bregalnica Štip - FK Pelister 2:2 (1:1)
19/04/2017 15:00 KF Shkëndija 79 - Vardar Skopje 0:1 (0:0)
15:00 FK Pelister - FK Bregalnica Štip 1:0 (0:0)
Final
17/05/2017 16:00 KF Shkëndija 79 - FK Pelister 3:4 (0:0, 0:0, 0:0) pso
Kup na Makedonija
Kup na Makedonija