Kaloyan of Bulgaria
The city was destroyed by Kaloyan of Bulgaria () in 1206 and rebuilt thereafter. In 1219, the city became the capital of the Crusader Duchy of Philippopolis, part of the Latin Empire. The Second Bulgarian Empire recovered the city in 1263, but lost it to Byzantine control before recapturing it in 1323. The Ottoman Empire conquered Philippopolis () in 1363 or 1364.