Kicevo was first mentioned as Uskana (Ωξάνα in Ancient Greek) in the reign of Perseus, king of Macedon during the Third Macedonian War (171–169 BC).

Kičevo was noted in one of the documents of the Byzantine emperor Basil II in 1018, and also mentioned by the Ohrid archbishop Theophilact in the 11th century.

After the downfall of the Serbian Empire the city was under the rule of Vukašin of Serbia of the Mrnjavčević family after which it passed to his son Prince Marko and finally to the Ottomans.

According to Toma Smiljanić-Bradina, the local Slavs of the region still lived in a semi-independent fashion as they did under the rule of Prince Marko retaining their status as "earthly lords" of their fortresses.

This semi-independent way of life persisted until the 15th century According to local folklore the inhabitants of the region also participated in the Christian rebellions during the Great Turkish War and were forced to flee after its failure.

[6] On August 2, 1903, the Christian citizens of Kičevo participated in the Ilinden Uprising, led by Arso Vojvoda and Yordan Piperkata.

During World War II, Kičevo was occupied by forces from Fascist Italy and ceded to the Italian protectorate of Albania.

On September 9, 1943, after the Armistice of Cassibile, Macedonian and Albanian partisan units disarmed the Italian garrison and took temporary control of the city.

The Brezi (belt) was not only used for decoration, but also as a symbol of the level of burrni (manhood) of its wearer as well as to store tobacco and related objects.

The brezi of grown married women is usually tighter and typically white, decorated with a variety of ornaments.

This monastery is actually an important site for the study of common cult of Christians and Muslims because it is visited by believers from both religions.