Rubuta ci gaba don wannan sakin layi - A cikin ƙarni na 13 da na 14, daular Byzantine, da Despotate na Epirus, da sarakunan Thessaly, da Daular Bulgaria sun yi jayayya da Makidoniya, amma sauye-sauyen kan iyakoki ba su haifar da manyan canje-canje na yawan jama'a ba. A shekara ta 1338, Daular Serbia ta ci shi, amma bayan Yaƙin Maritsa
a cikin 1371 yawancin shugabannin Serbia na Makidoniya sun yarda da ikon Ottoman. Bayan nasarar da Turks na Ottoman suka yi a kan Skopje a 1392, yawancin Makidoniya an haɗa su cikin Daular Ottoman.