Round of 32

15.09.2021 at 15:00 CET:
Detonit (2) – Makedonija GjP (1) 0:3
Pobeda (2) – Vardar (2) 1:1 (4:5 p.s.o.)
Besa 1976 (2) – Skopje (1) 1:1 (4:5 p.s.o.)
Lokomotiva (G) (2) – Ohrid (2) 0:2
Gostivar (2) – Renova (1) 0:4
Ljuboten (3) – Pelister (1) 0:9
Korabi (2) – Belasica (2) 1:2
Sloga 1934 (2) – Rabotnicki (1) 0:3
Novaci (3) – Tikvesh (1) 0:2
Sasa (2) – Struga (1) 0:2
Voska Sport (2) – Bregalnica (1) 0:1

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22.09.2021 at 15:00 CET:
Kit-Go (2) vs. Shkendija (1)
Nju Stars (3) vs. Borec (1)
Veleshta (2) vs. Shkupi (1)

Akademija Pandev (1) and Sileks (1) had a bye as finalists of the previous season.

Round of 16

Akademija Pandev (1)
Belasica (2)
Bregalnica (1)
Makedonija GjP (1)
Ohrid (2)
Pelister (1)
Rabotnicki (1)
Renova (1)
Sileks (1)
Skopje (1)
Struga (1)
Tikvesh (1)
Vardar (2)