The Byzantine emperor Basil II knew of its existence, historian Anna Komnena recorded the name as Devré in the Alexiad, and Feliks Petančić referred to it as Dibri in 1502.

Debar fell under the rule of the Ottoman Empire when local ruler Gjon Kastrioti died shortly after his four children were taken hostage.

[4][5] During the Ottoman-Albanian wars between 1443-1479 the Dibër region was the borderline between the Ottomans and the League of Lezhë led by Skanderbeg and became an area of continuous conflict.

[8] Of those that ended up in Istanbul, some of their number migrated to Albania, mainly to Tirana where the Dibran community formed an important segment of the capital city's population from 1920 onward and for some years thereafter.

Debar was annexed, along with most of Western North Macedonia, into the Italian-controlled Kingdom of Albania on 17 April 1941, following the Axis invasion of Yugoslavia during the Second World War.

Albania was officially a protectorate of Italy and therefore public administration duties were passed to Albanian authorities.

[9] After the cessation of hostilities with the end of WW2 and the establishment of communism in both Albania and Yugoslavia, Debar passed back into Yugoslav hands.

The Mijak School of woodcarving became noted for its artistic excellence, and an amazing example that can be seen today by tourists is the iconostasis in the nearby Monastery of Saint Jovan Bigorski, near the town of Debar.

Based on a folk poem, it deals with the exploits and heroic death of Kuzman Kapidan, a famous hero and protector of Christian people in the Debar region in their struggle with bandits.

As of 2018, Debar had one pizzeria for every 3,000 residents, and emigrants from the town had opened approximately 50 pizza restaurants in the United States.