1. Round
22/09/2020 14:30 Vardar Forino - Vardar Skopje 6:7 (0:1, 2:2) pso
23/09/2020 14:30 Makedonija GP - FK Pobeda Junior 5:4 pso
14:30 FK Ljuboten - FK Pelister 0:4 (0:0)
14:30 FK Sloga 1934 - KF Shkupi 1:2
14:30 KF Veleshta - FK Kožuf 1:2 (0:0)
14:30 FK Rosoman 83 - FK Belasica 1:5
14:30 FK Ohrid - FK Renova 0:4 (0:2)
14:30 Sileks Kratovo - FK Labuništa 3:0 (1:0)
14:30 Kamenica Sasa - FK Borec 3:1 (1:2, 2:2) pso
14:30 KF Gostivari - GFK Tikvesh 5:0 (1:0)
14:30 FK Vlazrimi 77 - FK Rabotnički 3:4 pso
17:00 FK Kit-Go Pehčevo - FK Skopje 2:1 (1:0)
Round of 16
21/10/2020 13:30 FK AP Brera Strumica - Vardar Skopje 1:0
13:30 Makedonija GP - Kamenica Sasa 6:0
13:30 KF Shkëndija 79 - KF Gostivari 1:0
13:30 KF Shkupi - FK Kit-Go Pehčevo 5:0
13:30 FK Kožuf - Sileks Kratovo 1:3
13:30 FC Struga - FK Rabotnički 4:3 (0:0, 0:0) pso
13:30 FK Bregalnica Štip - FK Belasica 0:1 (0:0)
13:30 FK Renova - FK Pelister 6:5 (0:1, 2:2) pso
Quarter-finals
25/11/2020 12:00 FK AP Brera Strumica - KF Shkupi 2:1 (1:0)
12:00 FK Belasica - Makedonija GP 1:4 (1:1)
12:00 Sileks Kratovo - KF Shkëndija 79 4:2 (0:0, 0:0) pso
12:00 FC Struga - FK Renova 1:0 (0:0)
Semi-finals
06/04/2021 12:00 Makedonija GP - FK AP Brera Strumica 1:3 (1:1)
07/04/2021 12:00 FC Struga - Sileks Kratovo 0:1 (0:0)
Final
19/05/2021 18:00 FK AP Brera Strumica - Sileks Kratovo 3:4 (0:0, 0:0, 0:0) pso
Kup na Makedonija
Kup na Makedonija