1. Round
08/08/2021 16:30 Akademija Pandev Akademija Pandev - FC Struga FC Struga -:-
08/08/2021 16:30 FK Bregalnica Štip FK Bregalnica Štip - KF Shkupi KF Shkupi -:-
08/08/2021 16:30 FK Rabotnički FK Rabotnički - FK Borec FK Borec -:-
08/08/2021 16:30 Makedonija GP Makedonija GP - FK Pelister FK Pelister -:-
08/08/2021 16:30 FK Renova FK Renova - FK Skopje FK Skopje -:-
08/08/2021 16:30 GFK Tikveš GFK Tikveš - KF Shkëndija 79 KF Shkëndija 79 -:-
2. Round
15/08/2021 16:00 Akademija Pandev Akademija Pandev - FK Rabotnički FK Rabotnički -:-
15/08/2021 16:00 FK Borec FK Borec - GFK Tikveš GFK Tikveš -:-
15/08/2021 16:00 KF Shkupi KF Shkupi - Makedonija GP Makedonija GP -:-
15/08/2021 16:00 FK Skopje FK Skopje - FK Bregalnica Štip FK Bregalnica Štip -:-
15/08/2021 16:00 KF Shkëndija 79 KF Shkëndija 79 - FK Renova FK Renova -:-
15/08/2021 16:00 FC Struga FC Struga - FK Pelister FK Pelister -:-
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