1. Round
14/09/2022 14:00 FK Belasica - KF Shkupi 1:3
14:00 FK Karaorman - KF Shkëndija 79 0:3
14:00 KF Gostivari - FK Pelister 0:1
14:00 Kamenica Sasa - Vardar Skopje 0:3
14:00 FK Kožuf - GFK Tikvesh 0:2
14:00 BVK Konjare - FK Rabotnički 0:5
14:00 Crno Buki ZL - FK Skopje 0:3 dec.
14:00 FK Teteks - FK AP Brera Strumica 0:6
14:00 Vardar Negotino - FC Struga 1:2
14:00 FK Karbinci - FK Pobeda Junior 0:6
14:00 FK Sloga 1934 - FK Bregalnica Štip 0:3
14:00 Zajazi Zajas - FK Voska Sport 0:3 dec.
14:00 FK Ljuboten - FK Renova 3:0 dec.
14:00 FK Fortuna - FK Borec 5:3
Round of 16
05/10/2022 13:00 FC Struga - FK Rabotnički 2:1
13:00 FK Bregalnica Štip - FK Pelister 1:0
13:00 Vardar Skopje - FK Fortuna 4:0
13:00 FK AP Brera Strumica - FK Ljuboten 9:0
13:00 KF Shkupi - FK Voska Sport 6:0
13:00 KF Shkëndija 79 - FK Skopje 5:0
13:00 GFK Tikvesh - Sileks Kratovo 0:1
19/10/2022 13:00 FK Pobeda Junior - Makedonija GP 0:2
Quarter-finals
09/11/2022 12:00 Sileks Kratovo - Vardar Skopje 3:2 (0:0, 0:0) pso
12:00 Makedonija GP - FK AP Brera Strumica 1:0 (0:0)
12:00 KF Shkupi - KF Shkëndija 79 0:3 dec.
12:00 FC Struga - FK Bregalnica Štip 2:0 (1:0)
Semi-finals
05/04/2023 14:00 FC Struga - Sileks Kratovo 1:0 (0:0)
14:00 KF Shkëndija 79 - Makedonija GP 3:4 (0:1, 1:1) pso
Final
20/05/2023 16:00 FC Struga - Makedonija GP 0:2 (0:1, 1:1, 1:1) pso
Kup na Makedonija
Kup na Makedonija