Kicevo was first mentioned as Uskana in the reign of Perseus, king of Macedon during the Third Macedonian War (171-169 BC).
The next written record of the town did not come until 1018 AD, under the name of Kicavis, noted in one of the documents of the Byzantine emperor Basil 2nd and also mentioned by the Ohrid archbishop Theophilact in 11th century. It is presumed that the today's name of the town originates from the name of this settlement populated by the Slavic Brsjaci (known as Bersites) tribe.
Kichevo was also known as Katin Grad (a city of Katina) in 13th-14th century, during the time of King Marko's rule over Macedonia, this town was a living place of his sister Katina.
When the region was conquered by the Ottoman Empire, Kicevo was turned into the military and administrative center of the region. Notable monument of that period is a clock tower built in the foothills of the nearby hill called Kicevsko Kale.
The activities of the IMRO (Internal Macedonian Revolutionary Organization) in the region of Kicevo were initiated by the priest Josif from the monastery of Bogorodica Precista near the city, supported by many teachers from the neighbouring villages. Priest Josif and Pere Toshev formed the first armed detachment in Kicevo in 1878, led by Duko Tasev. They were remembered as the leaders of the Brsjacka revolt in 1880.
On August 2nd, 1903, the citizens of Kicevo joined the struggle for Macedonian independence, led by Arso Vojvoda and Jordan Piperkata.
In 1919 Kicevo and the whole region were incorporated in the Kingdom of Serbs, Croats and Slovenes.
During the Second World War, Kicevo was occupied by forces from Fascist Italy. On September 11th 1943, Kicevo became the first liberated city in Macedonia. Special pride of this town are the heroes Mirko Mileski and Miha Mihajloski; as for the rest 555 partisans, a monument is raised at Kitino Kale.
The first schoold on Macedonian language was working in the Kicevo area in the village of Podvis.