1. Round
21/08/2013 Babi Štip - KF Gostivari 0:3 dec.
KF Shkupi - FK Teteks 0:3 dec.
16:00 Lokomotiva Skopje - Napredok Kičevo 1:5
16:30 Zajazi Zajas - Vardar Skopje 2:4
16:30 FK Karaorman - FK Pelister 0:5
16:30 FK Belasica - FK Turnovo 0:4
16:30 11 Oktomvri - FK Renova 0:4
16:30 FK Mogila - Sileks Kratovo 2:3
16:30 FK Korzo - Metalurg Skopje 0:1
16:30 FK Miravci - KF Rufeja 3:0
16:30 FK Borec - FK Drita 1:2
16:30 FK Ljuboten - Makedonija GP 0:3
16:30 FK Novaci 2005 - FK Gorno Lisiče 2:1
22/08/2013 16:00 Rabotnik Djumajlija - KF Shkëndija 79 0:7
16:00 FK Sateska Volino - FK Bregalnica Štip 0:3 dec.
16:00 Karbinci - FK Rabotnički 1:9
Round of 16
18/09/2013 15:00 Metalurg Skopje - Vardar Skopje 1:0
15:00 FK Turnovo - FK Bregalnica Štip 1:0
15:00 FK Teteks - FK Renova 2:2
15:00 FK Pelister - FK Miravci 2:0
15:00 FK Rabotnički - FK Novaci 2005 4:0
15:00 Sileks Kratovo - FK Drita 1:0
15:00 KF Gostivari - Napredok Kičevo 0:3
15:00 KF Shkëndija 79 - Makedonija GP 2:0
25/09/2013 14:30 Vardar Skopje - Metalurg Skopje 2:1 (2:1)
14:30 FK Novaci 2005 - FK Rabotnički 1:2 (1:1)
14:30 FK Drita - Sileks Kratovo 8:7 (1:0, 1:0) pso
14:30 Napredok Kičevo - KF Gostivari 1:2 (1:0)
15:00 FK Bregalnica Štip - FK Turnovo 3:0 pso
15:00 FK Renova - FK Teteks 4:5 pso
15:00 FK Miravci - FK Pelister 2:3 pso
15:00 Makedonija GP - KF Shkëndija 79 0:2
Quarter-finals
12/10/2013 13:00 FK Bregalnica Štip - KF Shkëndija 79 2:1
13/10/2013 13:00 FK Pelister - FK Rabotnički 1:0
13:00 FK Teteks - Napredok Kičevo 0:0
13:00 FK Drita - Metalurg Skopje 0:3
20/11/2013 12:00 Napredok Kičevo - FK Teteks 1:2
12:00 KF Shkëndija 79 - FK Bregalnica Štip 1:1
12:00 Metalurg Skopje - FK Drita 7:1
04/12/2013 12:00 FK Rabotnički - FK Pelister 2:0
Semi-finals
19/03/2014 13:00 FK Rabotnički - FK Bregalnica Štip 2:0 (1:0)
13:00 FK Teteks - Metalurg Skopje 0:0 (0:0)
16/04/2014 15:00 FK Bregalnica Štip - FK Rabotnički 4:5 (1:0, 2:0) pso
15:00 Metalurg Skopje - FK Teteks 1:0 (0:0)
Final
07/05/2014 19:00 FK Rabotnički - Metalurg Skopje 2:0 (1:0)
Kup na Makedonija
Kup na Makedonija