The logo of the Macedonian CupRound of 32

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

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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) vs. Osogovo (2)
Bregalnica (2) vs Makedonija GjP (1)
Shkupi (1) vs. Sileks (1)
Pelister (2) vs. Rabotnichki (1)
Tikvesh (2) vs. Renova (1)
Labunishta (2) vs. Ohrid (2)
Borec (1) vs. Struga (1)
Vardar (1) vs. Shkendija (1)

first leg: 25.09.2019 at 15.30 CET
return: 30.10.2019 at 13.30 CET