Round of 32

19.08.2019 at 17.00 CET
Novo Crnilishte (3) – Bregalnica (2) 0:22

20.08.2019 at 17.00 CET
Kit-Go (2) – Pelister (2) 1:1 (4:5 p.s.o.)
Ljuboten (3) – Tikvesh (2) 1:5

21.08.2019 at 17.00 CET
Fortuna (3) – Sileks (1) 0:4
Ohrid (2) – Belasica (2) 1:1 (5:4 p.s.o.)
Kozhuf (2) – Renova (1) 3:3 (5:6 p.s.o.)
Kravari (3) – Labunishta (2) 1:4
Teteks (3) – Shkupi (1) 1:5
Lokomotiva (3) – Struga (1) 1:5
Vlazrimi 77 (2) – Rabotnichki (1) 0:4
Prevalec (3) – Borec (1) 0:4
Osogovo (2) – Pobeda (2) 1:0
Gostivar (2) – Shkendija (1) 1:4

28.08.2019 at 17.00 CET
Sasa (2) – Vardar (1) 0:5

Akademija Pandev and Makedonija GjP had a bye.

Round of 16

Akademija Pandev (1) – Osogovo (2) 3:0, 4:1 (7:1 agg.)
Bregalnica (2) – Makedonija GjP (1) 1:0, 0:0 (1:0 agg.)
Shkupi (1) – Sileks (1) 0:0, 1:1 (1:1 agg.)
Pelister (2) – Rabotnichki (1) 1:1, 0:4 (1:5 agg.)
Tikvesh (2) – Renova (1) 0:2, 1:1* (1:3 agg.)
Labunishta (2) – Ohrid (2) 2:0, 3:2 (5:2 agg.)
Borec (1) – Struga (1) 0:0, 0:1 (0:1 agg.)
Vardar (1) – Shkendija (1) 2:2, 0:1 (2:3 agg.)

first leg: 25.09.2019 at 15.30 CET
return: 30.10.2019 at 13.30 CET, *31.10.2019 at 13.30 CET

Quarter-finals

Struga (1) – Renova (1) 0:0, 1:2 (1:2 agg.)
Bregalnica (2) – Labunishta (2) 1:0*, 4:1 (5:1 agg.)
Shkendija (1) – Rabotnichki (1) 1:1, 2:2 (3:3 agg.)
Shkupi (1) – Akademija Pandev (1) 0:1, 1:1 (1:2 agg.)

first leg: 04.12.2019 at 13.00 CET, *at 16.30 CET
return: 04.03.2020 at 14.00 CET

Semifinal

Akademija Pandev (1) – Bregalnica (2)
Shkendija (1) – Struga (1)

first leg: 08.04.2020 at 15.30 CET
return: 06.05.2020 at 16.00 CET

*Due to the COVID-19 pandemic the season forcibly ended.