Round of 32

14.09.2021 at 15:00 CET:
Belasica (2) – Shkupi (1)
Gostivar (2) – Pelister (2)
Teteks (2) – Akademija Pandev (1)
Sloga 1934 (2) – Bregalnica (1)
Sasa (2) – Vardar (2)
Kozhuf (2) – Tikvesh (1)
Vardar (N) (3) – Struga (1)
Karbinci (3) – Pobeda (1)
Zajazi (3) – Voska Sport (2)
Fortuna (3) – Borec (2)
Ljuboten (3) – Renova (1) 3:0 awarded
BVK Konjari (3) – Rabotnichki (1)
Crno Buki ZL (3) – Skopje (1)
Karaorman (2) – Shkendija (1)

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Makedonija GjP (1) and Sileks (1) have a bye as finalists of the previous season.

Round of 16

Ljuboten (3)
Makedonija GjP (1)
Sileks (1)