Round of 16
24/09/2014 14:30 KF Shkëndija 79 KF Shkëndija 79 - Vardar Skopje Vardar Skopje 2:1
24/09/2014 14:30 FK Kožuf - Napredok Kičevo Napredok Kičevo 0:0
24/09/2014 14:30 FK Pelister FK Pelister - FK Rabotnički FK Rabotnički 0:0
24/09/2014 14:30 FK Gostivar FK Gostivar - FK Renova FK Renova 1:4 (1:2)
24/09/2014 14:30 FK Pobeda Junior FK Pobeda Junior - FK Drita FK Drita 1:0
24/09/2014 14:30 FK Turnovo FK Turnovo - FK Bregalnica Štip FK Bregalnica Štip 0:0
24/09/2014 14:30 Sileks Kratovo Sileks Kratovo - FK Gorno Lisice FK Gorno Lisice 1:1
24/09/2014 14:30 KF Shkupi KF Shkupi - FK Teteks FK Teteks 1:1
14/10/2014 11:00 FK Renova FK Renova - FK Gostivar FK Gostivar 1:0 (1:0)
14/10/2014 14:00 Napredok Kičevo Napredok Kičevo - FK Kožuf 1:5 (0:2)
14/10/2014 14:00 FK Drita FK Drita - FK Pobeda Junior FK Pobeda Junior 3:1 (0:0, 1:1) pso
14/10/2014 14:00 FK Bregalnica Štip FK Bregalnica Štip - FK Turnovo FK Turnovo 3:4 (0:0, 0:0) pso
14/10/2014 14:00 FK Gorno Lisice FK Gorno Lisice - Sileks Kratovo Sileks Kratovo 0:0 (0:0)
14/10/2014 14:00 FK Teteks FK Teteks - KF Shkupi KF Shkupi 1:0 (1:0)
21/10/2014 13:30 FK Rabotnički FK Rabotnički - FK Pelister FK Pelister 3:1 (1:0)
22/10/2014 14:00 Vardar Skopje Vardar Skopje - KF Shkëndija 79 KF Shkëndija 79 3:0 (3:0)