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 In that period the richer citizens constructed houses, many of which can still be seen in the Architectural reserve "Old Plovdiv". The city was the capital of Rumelia Province between 1364–1864, and of Edirne province between 1864–1878 under Ottoman Rule. Plovdiv played a role in the struggle for Church independence. Plovdiv became the center of that struggle with leaders such as Nayden Gerov, Dr Valkovich, and Joakim Gruev. In 1836 the first Bulgarian school was inaugurated and in 1850 modern secular education began with the St Cyril and Methodius school. On 11 May 1858 the city celebrated the saints' day