1. Runde
20.09.2023 15:00 Young Team Struga - FK Pobeda Junior 4:3 (0:0) i.E.
15:00 FK Novaci 2005 - FK Bregalnica Štip 0:8 (0:4)
15:00 KF Bashkimi - FK Skopje 4:3 (0:1) i.E.
15:00 KF Arsimi - GFK Tikvesh 1:2 (0:2)
15:00 FK Kožuf - Akademija Pandev 0:2 (0:0)
15:00 FK Ohrid - FK Detonit Plačkovica 2:0 (1:0)
15:00 FK Belasica - KF Gostivari 0:3 (0:0) i.E.
15:00 BVK Konjare - KF Shkupi 0:8 (0:3)
15:00 KF Besa Dobërdoll - Vardar Skopje 4:5 (1:1) i.E.
15:00 FK Teteks - FK Rabotnički 0:3 (0:0)
15:00 FK Vlazrimi 77 - FK Pelister 0:4 (0:2)
15:00 Karbinci - FK Voska Sport 0:10 (0:4)
Achtelfinale
25.10.2023 14:00 Vardar Skopje - Makedonija GP 0:1 (0:0)
14:00 FK Bregalnica Štip - Young Team Struga 11:0 (6:0)
14:00 FK Rabotnički - KF Shkëndija 79 3:2 (1:2)
14:00 Sileks Kratovo - KF Bashkimi 3:2 (2:0)
14:00 FK Pelister - GFK Tikvesh 0:1 (0:0)
14:00 Akademija Pandev - KF Gostivari 5:4 (0:0) i.E.
14:00 KF Shkupi - FK Ohrid 4:0 (1:0)
14:00 FK Voska Sport - FC Struga 4:1 (0:0) i.E.
Viertelfinale
08.11.2023 13:00 GFK Tikvesh - Akademija Pandev 6:5 (0:1, 1:1) i.E.
13:00 FK Bregalnica Štip - FK Voska Sport 0:1 (0:0)
13:00 Makedonija GP - Sileks Kratovo 1:0 (0:0)
09.11.2023 13:00 FK Rabotnički - KF Shkupi 0:1 (0:1)
Halbfinale
02.04.2024 15:00 KF Shkupi - GFK Tikvesh 0:0 (0:0)
03.04.2024 15:00 FK Voska Sport - Makedonija GP 2:0 (2:0)
17.04.2024 15:00 GFK Tikvesh - KF Shkupi 5:3 (0:0, 0:0) i.E.
15:00 Makedonija GP - FK Voska Sport 2:1 (1:1)
Finale
22.05.2024 19:00 GFK Tikvesh - FK Voska Sport -:-
Kup na Makedonija
Kup na Makedonija
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