The schedule and competitive pairings for the Round of 32 of the Macedonia Cup for the 2026/27 season have been determined, in accordance with the teams’ standings in the competitive season 2025/26. Fifteen matches will be played in this round, while Silex, as the winner of the 2025/26 Macedonia Cup, has a bye in the Round of 32 and will advance directly to the Round of 16.
PAIRINGS – ROUND OF 32:
Ovche Pole Sveti Nikole – Vardar
Pobeda Valandovo – Struga Trim Lum
Kroshu Sport Bitola – Tikvesh 1930
Mogila 2023 – Aresimi 1973
BVK Konjari – Bashkimi 1947
Studenichani – Pelister
Venets Negotino – AP Brera Strumica
Vllaznimi Junior – Makedonija GP 1932
Vardar Negotino – Rabotnichki
Kamenica Sasa – Shkupi 1927
Teteks 1953 – Bregalnitsa 2008
Kozhuf Gevgelija – Skopje
Detonit Plachkovica – Shkendija 77 Arachinovo
Novaci 2005 – Ohrid Lychnidos
Osogovo – Belasica
Bye in the round of 32: Silex
The round-of-32 matches will be played on 1 or 2 September 2026. The exceptions are the Kroshu Sport Bitola – Tikvesh and Mogila – Aresimi matches, which will be played on 24 September due to the participation of a selection from Bitola in the UEFA Regions' Cup qualifiers in Bosnia and Herzegovina.
The home teams will be able to organize the matches at stadiums approved at least for hosting matches from Second MFL.
In accordance with the FFM Cup Competition Regulations for the 2026/27 season, up to the final of the Macedonia Cup, there will be only one match, meaning there will be no second legs. If the match ends in a draw after the 90 minutes of regular time, a penalty shootout will begin immediately and continue until a winner is determined.
The draw for the round of 16 of the Macedonia Cup will be conducted in accordance with the Cup Competition Regulations for the 2026/27 season.
