1. Round
19/08/2019 16:00 FK Novo Crnilishte - FK Bregalnica Štip 0:22
20/08/2019 16:00 FK Ljuboten - GFK Tikvesh 1:5
16:00 FK Kit-Go Pehčevo - FK Pelister 4:5 pso
21/08/2019 16:00 FK Fortuna - Sileks Kratovo 0:4
16:00 FK Ohrid - FK Belasica 5:4 pso
16:00 FK Kravari - FK Labuništa 1:4
16:00 KF Gostivari - KF Shkëndija 79 1:4
16:00 FK Osogovo - FK Pobeda Junior 1:0
16:00 FK Vlazrimi 77 - FK Rabotnički 0:4
16:00 Prevalec - FK Borec 0:4
16:00 Lokomotiva Skopje - FC Struga 1:5
16:00 FK Kožuf - FK Renova 5:6 pso
16:00 FK Teteks - KF Shkupi 1:5
28/08/2019 16:00 Kamenica Sasa - Vardar Skopje 0:5
Round of 16
25/09/2019 14:30 Akademija Pandev - FK Osogovo 3:0
14:30 FK Bregalnica Štip - Makedonija GP 1:0
14:30 KF Shkupi - Sileks Kratovo 0:0
14:30 FK Pelister - FK Rabotnički 1:1
14:30 GFK Tikvesh - FK Renova 0:2
14:30 FK Labuništa - FK Ohrid 2:0
14:30 FK Borec - FC Struga 0:0
14:30 Vardar Skopje - KF Shkëndija 79 2:2
30/10/2019 12:30 FK Osogovo - Akademija Pandev 1:4
12:30 Makedonija GP - FK Bregalnica Štip 0:0
12:30 Sileks Kratovo - KF Shkupi 1:1
12:30 FK Rabotnički - FK Pelister 4:0
12:30 FK Ohrid - FK Labuništa 2:3
12:30 FC Struga - FK Borec 1:0
12:30 KF Shkëndija 79 - Vardar Skopje 1:0
31/10/2019 12:30 FK Renova - GFK Tikvesh 1:1
Quarter-finals
04/12/2019 12:00 KF Shkëndija 79 - FK Rabotnički 1:1
12:00 KF Shkupi - Akademija Pandev 0:1
12:00 FC Struga - FK Renova 0:0
15:30 FK Bregalnica Štip - FK Labuništa 1:0
04/03/2020 13:00 FK Rabotnički - KF Shkëndija 79 2:2 (0:1)
13:00 Akademija Pandev - KF Shkupi 1:1 (0:0)
13:00 FK Renova - FC Struga 1:2 (1:1)
13:00 FK Labuništa - FK Bregalnica Štip 1:4 (0:3)
Semi-finals
08/04/2020 FC Struga - KF Shkëndija 79 dnp
Akademija Pandev - FK Bregalnica Štip dnp
06/05/2020 KF Shkëndija 79 - FC Struga dnp
FK Bregalnica Štip - Akademija Pandev dnp
Kup na Makedonija
Kup na Makedonija