Round of 32

02.09.2026 at 16.30 CET
Pobeda (V) (3) – Struga (1) 1:10
Studeniçan (3) – Pelister (2) 1:6
Venec (3) – Brera Strumica (2) 0:8
Vlaznimi Junior (3) – Makedonija GjP (2) 0:14

03.09.2026 at 16.30 CET
Ovche Pole (3) – Vardar (1) 0:5

09.09 at 16.00 CET
BVK Konjare (3) – Bashkimi (1) 0:5
Sasa (3) – Shkupi (2) 1:0
Teteks (2) – Bregalnica (1) 1:4
Kozhuf (2) – Skopje (1) 0:1
Det. Plachkovica (2) – Shkëndija 77 (1) 1:3
Novaci (2) – Ohrid Lychnidos (2) 1:0
Osogovo (2) – Belasica (2) 1:3

24.09.2026 at 15.30 CET
Mogila (3) – Arsimi (1) 0:12

06.10.2026 at 15.00 CET
KroSchu Sport (3) – Tikvesh (1) 0:13

14.10.2026 at 15.00 CET
Vardar (N) (3) – Rabotnichki (2)

Sileks (1) has a bye as title holder.
Shkëndija was banned from entering the Cup for not showing up for the medal ceremony at previous season’s final.

Round of 16

Arsimi (1)
Bashkimi (1)
Belasica (2)
Bregalnica (1)
Brera Strumica (2)
Makedonija GjP (2)
Novaci (2)
Pelister (2)
Sasa (3)
Shkëndija 77 (1)
Sileks (1)
Skopje (1)
Struga (1)
Tikvesh (1)
Vardar (1)