1. Round
15/09/2021 14:00 FK Detonit Junior FK Detonit Junior - Makedonija GP Makedonija GP 0:3
15/09/2021 14:00 FK Pobeda Junior FK Pobeda Junior - Vardar Skopje Vardar Skopje 4:5 pso
15/09/2021 14:00 KF Besa Dobërdoll KF Besa Dobërdoll - FK Skopje FK Skopje 4:5 (0:0, 1:1) pso
15/09/2021 14:00 Lokomotiva Gradsko Lokomotiva Gradsko - FK Ohrid FK Ohrid 0:2
15/09/2021 14:00 FK Gostivar FK Gostivar - FK Renova FK Renova 0:4
15/09/2021 14:00 FK Ljuboten FK Ljuboten - FK Pelister FK Pelister 0:9
15/09/2021 14:00 KF Korabi KF Korabi - FK Belasica FK Belasica 1:2
15/09/2021 14:00 FK Sloga 1934 FK Sloga 1934 - FK Rabotnički FK Rabotnički 0:3
15/09/2021 14:00 FK Novaci 2005 FK Novaci 2005 - GFK Tikveš GFK Tikveš 0:2
15/09/2021 14:00 Kamenica Sasa Kamenica Sasa - FC Struga FC Struga 0:2
15/09/2021 14:00 FK Voska Sport FK Voska Sport - FK Bregalnica Štip FK Bregalnica Štip 0:1
22/09/2021 14:00 FK Kit-Go Pehčevo FK Kit-Go Pehčevo - KF Shkëndija 79 KF Shkëndija 79 0:2
22/09/2021 14:00 FK New Stars FK New Stars - FK Borec FK Borec 1:4
22/09/2021 14:00 KF Veleshta KF Veleshta - KF Shkupi KF Shkupi 0:1