The first information about the town was found in Turkish records from 1519 in which Kumanovo was described as a settlement of 52 families and 300 inhabitants. In 1660 the Ottoman traveler Evlia Chelebi wrote:

‘The town of Kumanovo is situated on the territory of Skopje district and is an entire province. The town is ‘decorated’ with lots of rivers and 600 tiled houses. The mosque, situated on the ‘charshia’ (market), is lovely. It has ‘teke’, ‘medrese’, ‘hammam’ (Turkish baths), a sufficient number of shops and water-mills and the climate is nice and pleasant. There are plenty of vineyards and gardens.’

In the beginning of 20th century Kumanovo was a mixed Bulgarian- Turkish town within the Ottoman Empire and the Christian population was predominant under the supremacy of the Bulgarian exarchate. According to information taken by the secretary of the exarchate Dimitur Mishev („La Macédoine et sa Population Chrétienne“) in 1905 in Kumanovo there lived 7 032 Bulgarians - exarchate supporters, 1 569 Bulgarians - patriarchate Serb supporters, 5 Greeks, 150 Wallachian and 180 gipsies. Bulgarian primary and junior high schools, Serbian primary and junior high schools, as well as Wallachian primary school are in function in the town.

Nowadays Kumanovo is the second largest town in Republic of Macedonia and according to the census taken in 2002 thete are 70 842 residents.

In February 2009 a written statement of intent on cooperation between the two towns was signed.