Plovdiv city was possibly at times a vassal of Bulgaria or Venice. Ivan Asen II conquered the duchy finally in 1230 but the city had possibly been conquered earlier. Afterwards, Plovdiv was conquered by Byzantium. According to some information, by 1300 Plovdiv was a possession of Theodore Svetoslav of Bulgaria. It was conquered from Byzantium by George Terter II of Bulgaria in 1322. Andronikos III Palaiologos unsuccessfully besieged the city, but a treaty restored Byzantine rule once again in 1323. In 1344 the city and eight other cities were surrendered to Bulgaria by the regency for John V Palaiologos as the
History of Plovdiv BC, Plovdiv was conquered by Philip II of Macedon, the father of Alexander the Great, who renamed it "Φιλιππόπολις", "Philippopolis" or "the city of Philip" in his own honour. Later, it was reconquered by the Thracians who called it "Pulpudeva" (from Philipopolis). In 72 BC, Plovdiv was seized by the Roman general Terentius Varo Luculus. The city was incorporated into the Roman Empire, where it was called "Trimontium" ("City of Three Hills") and served as capital of the province of Thrace. Thrimontium was an important crossroad for the Roman Empire and was called "The largest and most beautiful of all