1. Round
22/08/2018 16:00 KF Korabi - FK Borec 1:0
16:00 FK Vlazrimi 77 - FK Belasica 0:4
16:00 Vardar Negotino - FK Skopje 1:3
16:00 FK Fortuna - FK Rabotnički 0:6
16:00 FK Labuništa - Akademija Pandev 1:3
16:00 FK Kit-Go Pehčevo - KF Shkupi 2:0
16:00 Poeševo - FK Bregalnica Štip 0:4
16:00 Vardar Forino - Vardar Skopje 0:4
16:00 FK Osogovo - FK Pelister 0:1
16:00 FK Teteks - KF Gostivari 0:1
16:00 Bratstvo-Vlaznimi - Sileks Kratovo 0:7
16:00 GFK Tikvesh - FK Renova 2:1
16:00 Prevalec - Makedonija GP 0:2
29/08/2018 16:00 FC Struga - FK Pobeda 1:2
12/09/2018 14:30 FK Kožuf - KF Shkëndija 79 0:2
2. Round
19/09/2018 14:30 GFK Tikvesh - FK Rabotnički 0:1
14:30 KF Gostivari - FK Pobeda 1:2
14:30 Vardar Skopje - Makedonija GP 1:1
14:30 FK Skopje - Sileks Kratovo 0:2
14:30 KF Shkëndija 79 - FK Kit-Go Pehčevo 2:0
14:30 FK Bregalnica Štip - Akademija Pandev 2:6
14:30 FK Pelister - FK Belasica 0:2
03/10/2018 14:00 FK Rabotnički - GFK Tikvesh 1:1 (0:0)
14:00 FK Pobeda - KF Gostivari 4:1 (3:1)
14:00 Makedonija GP - Vardar Skopje 2:1 (1:1)
14:00 Sileks Kratovo - FK Skopje 2:1 (0:1)
14:00 FK Kit-Go Pehčevo - KF Shkëndija 79 0:5 (0:3)
14:00 Akademija Pandev - FK Bregalnica Štip 0:1 (0:1)
14:00 FK Belasica - FK Pelister 3:1
Quarter-finals
07/11/2018 12:00 KF Shkëndija 79 - FK Pobeda 0:1 (0:1)
12:00 Sileks Kratovo - FK Belasica 0:2 (0:0)
12:00 Akademija Pandev - KF Korabi 3:1 (2:1)
12:00 Makedonija GP - FK Rabotnički 1:0 (0:0)
05/12/2018 12:00 FK Pobeda - KF Shkëndija 79 2:0 (1:0)
12:00 FK Belasica - Sileks Kratovo 2:0 (0:0)
12:00 KF Korabi - Akademija Pandev 1:6 (1:2)
12:00 FK Rabotnički - Makedonija GP 0:1 (0:0)
Semi-finals
27/02/2019 13:00 FK Belasica - Makedonija GP 0:1 (0:1)
06/03/2019 13:00 Akademija Pandev - FK Pobeda 3:1 (0:0)
10/04/2019 14:30 Makedonija GP - FK Belasica 1:0 (0:0)
14:30 FK Pobeda - Akademija Pandev 1:3 (1:0)
Final
22/05/2019 17:30 Makedonija GP - Akademija Pandev 2:4 (1:1, 2:2, 2:2) pso
Kup na Makedonija
Kup na Makedonija