Round of 32

14.09.2022 at 15:00 CET:
Belasica (2) – Shkupi (1) 1:3
Gostivar (2) – Pelister (2) 0:1
Teteks (2) – Akademija Pandev (1) 0:6
Sloga 1934 (2) – Bregalnica (1) 0:3
Sasa (2) – Vardar (2) 0:3
Kozhuf (2) – Tikvesh (1) 0:2
Vardar (N) (3) – Struga (1) 1:2
Karbinci (3) – Pobeda (1) 0:6
Zajazi (3) – Voska Sport (2) 0:3 awarded
Fortuna (3) – Borec (2) 5:3
Ljuboten (3) – Renova (1) 3:0 awarded
BVK Konjari (3) – Rabotnichki (1) 0:5
Crno Buki ZL (3) – Skopje (1) 0:3 awarded
Karaorman (2) – Shkendija (1) 0:3

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

Round of 16

05.10.2022 at 14:00 CET:
Struga (1) – Rabotnichki (1) 2:1
Bregalnica (1) – Pelister (2) 1:0
Vardar (2) – Fortuna (3) 4:0
Akademija Pandev (1) – Ljuboten (3) 9:0
Shkupi (1) – Voska Sport (2) 6:0
Shkendija (1) – Skopje (1) 5:0
Tikvesh (1) – Sileks (1) 0:1

19.10.2021 at 14:00 CET:
Pobeda (1) – Makedonija GjP (1) 0:2

Quarter-finals

09.11.2022 at 13:00 CET:

Sileks (1) vs. Vardar (2) 0:0 (3:2 p.s.o.)
Struga (1) vs. Bregalnica (1) 2:0
Makedonija GjP (1) vs. Akademija Pandev (1) 1:0
Shkupi (1) vs. Shkendija (1) 0:3 awarded

Semifinals:

Makedonija GjP (1)
Shkendija (1)
Sileks (1)
Struga (1)