[3] Along with Dimitrovgrad (Tsaribrod), Bosilegrad is an economic and cultural centre of Serbia's ethnic Bulgarian community.

On May 15, 1917, Serbian paramilitaries (Chetniks) under the command of Kosta Pećanac crossed the old Bulgarian border and, as part of the Toplica Uprising, captured Bosilegrad, which they then burned.

Then Pećanac and his band withdrew to Kosovo, which was controlled by the Austro-Hungarian Army.

The Kingdom of Serbs, Croats and Slovenes gained some territory from Bulgaria as part of the Treaty of Neuilly-sur-Seine, following the invasion and occupation of part of the Kingdom of Serbia by Bulgaria and subsequent Allied defeat of the Central Powers in the First World War.

Other minor ethnic groups are Serbs and Roma people.