Presumably, Starobilsk traces its heritage to the settlement of Bielska Sloboda which originally might have been named after Okolnichy Bogdan Belsky of Litvin Bielsky family who at that time was a subject of the Grand Duchy of Moscow.

[citation needed] Bielsky arrived at the banks of Siversky Donets to build a fortress at the southern borders Tsare-Borisov (after Muscovite Tsar Boris Godunov) which was erected not far away in 1598–1600.

Being runaway serfs, the Tsarist government allowed them to settle in the military frontier with the Crimean realm to carry out border guard functions.

After the place became populated with serfs from the central regions of today's Russia, the Tsarist government took measures to find and return those fugitives.

Trying to meet the demands of Russian landlords who repeatedly turned to the Tsar with complaints and requests to return fugitives, on 6 July 1707 Peter the Great issued an edict (ukase) about the search of "newly arrived from Rus all ranks of people".

Founded on 12 October 1851, Starobilsk "Joy of All Who Sorrows" Convent (Свято-Скорботний жіночий монастир) became a spiritual center for the region.

A photograph in the City Regional Museum (Старобільський краєзнавчий музей) shows Anarchist leader Nestor Makhno addressing the people of Starobilsk from a balcony on the main square in 1919.

In 1994, their bodies were moved to the Polish War Quarter built by the Council for the Protection of Struggle and Martyrdom Sites at the Chmyrivka cemetery.

[2][3][4][5][6] The German Wehrmacht entered Starobilsk in late 1942, and evacuated nine months later, destroying much of the city but neglecting to dynamite the milk factory.

[citation needed] On 6 March 2022, hundreds of locals gathered and took down the flag of the so-called Luhansk People's Republic, burning it and singing the Ukrainian national anthem.

On 13 September, Ukrainian Governor of Luhansk Oblast, Serhiy Haidai, stated that Russian forces had fled Starobilsk adding that the city was "practically empty".