1. Round
15/09/2021 14:00 FK Detonit Junior - Makedonija GP 0:3
14:00 FK Pobeda Junior - Vardar Skopje 4:5 pso
14:00 KF Besa Dobërdoll - FK Skopje 4:5 (0:0, 1:1) pso
14:00 Lokomotiva Gradsko - FK Ohrid 0:2
14:00 KF Gostivari - FK Renova 0:4
14:00 FK Ljuboten - FK Pelister 0:9
14:00 KF Korabi - FK Belasica 1:2
14:00 FK Sloga 1934 - FK Rabotnički 0:3
14:00 FK Novaci 2005 - GFK Tikvesh 0:2
14:00 Kamenica Sasa - FC Struga 0:2
14:00 FK Voska Sport - FK Bregalnica Štip 0:1
22/09/2021 14:00 FK Kit-Go Pehčevo - KF Shkëndija 79 0:2
14:00 FK New Stars - FK Borec 1:4
14:00 KF Veleshta - KF Shkupi 0:1
Round of 16
20/10/2021 13:00 FC Struga - FK Borec 5:4 pso
13:00 FK AP Brera Strumica - Makedonija GP 3:5 pso
13:00 KF Shkëndija 79 - FK Renova 5:0
13:00 FK Bregalnica Štip - FK Ohrid 4:0
13:00 FK Belasica - Sileks Kratovo 2:4
13:00 FK Pelister - FK Rabotnički 5:4 pso
13:00 KF Shkupi - GFK Tikvesh 1:0
13:00 Vardar Skopje - FK Skopje 4:2 pso
Quarter-finals
01/12/2021 12:00 Sileks Kratovo - FK Bregalnica Štip 5:4 (0:0, 1:1) pso
12:00 KF Shkëndija 79 - FC Struga 3:4 (0:0, 0:0) pso
12:00 Makedonija GP - KF Shkupi 4:1 (0:0, 0:0) pso
15/12/2021 12:00 FK Pelister - Vardar Skopje 3:2 (0:0, 0:0) pso
Semi-finals
20/04/2022 15:00 FK Pelister - Sileks Kratovo 0:1 (0:1)
15:00 FC Struga - Makedonija GP 2:4 (0:0, 0:0) pso
Final
20/05/2022 17:00 Sileks Kratovo - Makedonija GP 3:4 (0:0, 0:0, 0:0) pso
Kup na Makedonija
Kup na Makedonija