It was founded in 1137 by the Smolensk prince Rostislav Mstislavitch, hence the name. Roslavl was chartered under Lithuanian rule in 1408. Under Polish rule Roslavl was part of the Smolensk Voivodeship. In the 1667 truce of Andrusovo the town was ceded from Poland to Russia. During World War II, the town was occupied by the German Army from August 3, 1941 to September 25, 1943.