1. Round
19/08/2014 16:00 11 Oktomvri 11 Oktomvri - KF Shkupi KF Shkupi 0:9 (0:4)
20/08/2014 16:00 FK Fortuna - FK Turnovo FK Turnovo 0:8 (0:0)
20/08/2014 16:00 Rabotnik Djumajlija - Sileks Kratovo Sileks Kratovo 0:3
20/08/2014 16:00 FK Miravci FK Miravci - Makedonija GP Makedonija GP 2:1
20/08/2014 16:00 FK Goblen - FK Teteks FK Teteks 0:3 (0:1)
20/08/2014 16:00 FK Novaci 2005 FK Novaci 2005 - FK Gostivar FK Gostivar 0:5 (0:2)
20/08/2014 16:00 Bregalnica Delcevo - FK Drita FK Drita 1:4
20/08/2014 16:00 FK Belasica FK Belasica - Napredok Kičevo Napredok Kičevo 2:4 (1:1, 1:1) pso
20/08/2014 16:00 Kamenica Sasa Kamenica Sasa - FK Renova FK Renova 0:2
20/08/2014 16:00 FK Vlaznimi FK Vlaznimi - Vardar Skopje Vardar Skopje 1:9 (0:2)
20/08/2014 16:00 Mladost Carev Dvor - FK Bregalnica Štip FK Bregalnica Štip 0:1
20/08/2014 16:00 FK Pobeda Junior FK Pobeda Junior - Metalurg Skopje Metalurg Skopje 3:2
21/08/2014 16:00 FK Vulkan - FK Pelister FK Pelister 0:2 (0:0)