Albanian sources claim that the town (initially a village) obtained its name from Bahti Beg Gjinolli of Gjinaj clan that ruled the region of Vushtrri (Llap and Drenica), and populated this area in the 18th century (around 1750).

[citation needed] However, there is no definite evidence to support this claim and in fact no one can confirm who the first real inhabitants were or when they first settled.

Gjilan as a town developed in addition to the extinction of Novo Brdo, which in the Middle Ages was one of the cities and the largest commercial, economic and mining centers in the Balkans.

The feudal family "Gjinaj" in the second half of the nineteenth century transferred their headquarters from Novo Brdo and built their own houses in the place where Gjilani is now located.

[11]In 1985, Gjilan was the site of an incident involving a Serbian farmer who had a glass bottle shatter inside his rectum, before going to the local police and blaming two Kosovar Albanians.

[13][14][15] In 2020, the cities of Gjilan and Kumanovo, North Macedonia came closer through a new border point which was built in the village of Stançiq.

There are three small rivers, Mirusha, Banja and Stanishori, which join and flow to Binačka Morava, west of the Uglara village.

According to the most recent census in 2024, Gjilan is home to 82,901 residents, making it the fourth biggest city in Kosovo.

[20] The population of Gjilan has always been mixed, but with a predominant majority of Albanians in both periods during Turkish and Serbian-Yugoslav rule.

The population consisted of 87,814 Albanians (97.38%), 978 Turks (1.08%), 624 Serbs (0.69%), 121 (0.13%) Bosniaks, and 541 (0.60%) from smaller groups, including Roma, Ashkali, Gorani and Egyptians.

It gathers thousands of artists and art lovers from all the Albanian lands, who for three consecutive weeks transform the city into a cultural metropolis.

It was exactly the tenth anniversary without these three martyrs of freedom and from coincidence of these murders in a same date on 11 January, this event got this name "Flaka e Janarit".

Хаџи Калфа (прва половина 17. века) помиње неко место Мораву, на 17 дана од Цариграда.

Janjeva, Novo Brdo and Kaca-...""Горња Морава се под турском управом звала само Морава, а протезала се западно од линије с. Жегра–Будрига–Церница, тако да је Гњилане остајало у области Топонице, чије је обласно средиште било Ново Брдо."

Старо Гњилане налазило се у Петиковиди (Петковици) предграђу данашњег насеља које је подигнуто на месту" "From the Ottoman Defter (1455) it is seen that it was inhabited by Serbs and that in it the priest Bozidar served.

Old Gnjilane was located in Petikovida (Petkovica) suburb of today's settlement which was created in that place""Гњилане је дакле могло постати тек после овог кадије, око 1780 године, тако да је после 20–25 година, на крају 18 века, могло бити велико село – варошица.