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===Middle Ages=== [[File:Monument of Khan Krum in Plovdiv.jpg|left|thumb|220px|Monument of [[Krum of Bulgaria|Krum]] in Plovdiv, who was the first Bulgarian ruler to capture Plovdiv.]] The [[Slavic peoples|Slavs]] had fully settled in the area by the middle of the 6th century. This was done peacefully as there are no records for their attacks.<ref>{{Cite book |last=Dimitrov |first=B. |title=The Bulgarians – the first Europeans |publisher=University press "St Climent of Ohrid" |location=Sofia |page=25 |language=bg |isbn=954-07-1757-4 |year=2002 }}</ref> With the establishment of [[Bulgaria]] in 681, Philippoupolis, the name of the city then, became an important border fortress of the [[Byzantine Empire]]. It was captured by Khan [[Krum of Bulgaria|Krum]] in 812, but the region was fully incorporated into the [[First Bulgarian Empire|Bulgarian Empire]] in 834 during the reign of Khan [[Malamir of Bulgaria|Malamir]].<ref>Аndreev, J. ''The Bulgarian Khans and Tsars'' (''Balgarskite hanove i tsare'', ''Българските ханове и царе''), Veliko Tarnovo, 1996, p. 66 {{ISBN|954-427-216-X}}.</ref> It was reconquered by the [[Byzantine Empire]] in 855–856 for a short time until it was returned to [[Boris I of Bulgaria]].<ref>Gjuzelev, p. 130 (Gjuzelev, V., (1988) Medieval Bulgaria, Byzantine Empire, Black Sea, Venice, Genoa (Centre Culturel du Monde Byzantin). Published by Verlag Baier).</ref><ref>Bulgarian Historical Review, p. 9 (Bulgarian Historical Review (2005), United Center for Research and Training in History, published by Publishing House of the Bulgarian Academy of Sciences, v.33:no.1–4).</ref> From Philippopolis, the influence of [[Dualistic cosmology|dualistic]] doctrines spread to Bulgaria forming the basis of the [[Bogomil]] heresy. The city remained in Bulgarian hands until 970.<ref>Делев, "Българската държава и общество при управлението на цар Петър", ''История и цивилизация за 11. клас'', 2006.</ref> However, the city is described at the time of [[Constantine VII]] in the 10th century as being within the Byzantine province ([[theme (Byzantine district)|theme]] of [[Macedonia (theme)|Macedonia]]).{{citation needed|date=August 2020}} Philippopolis was captured by the Byzantines in 969, shortly before it was sacked by the ruler of [[Kievan Rus'|Rus']] [[Sviatoslav I of Kiev]] who impaled 20,000 citizens.<ref>Fine, pp. 160–161, 186: John V. A. Fine Jr., The Early Medieval Balkans, Ann Arbor, 1983.</ref> Before and after the Rus' massacre, the city was settled by [[Paulician]] heretics transported from Syria and Armenia to serve as military settlers on the European frontier with Bulgaria. Aime de Varennes in 1180 encountered the singing of Byzantine songs in the city that recounted the deeds of Alexander the Great and his predecessors over 1300 years before.<ref>Vacalopoulos, Apostolos E. ''Origins of the Greek Nation''. (New Brunswick, New Jersey: [[Rutgers University Press]], 1970) p. 22.</ref> Byzantine rule was interrupted by the [[Third Crusade]] (1189–1192) when the army of the [[Holy Roman Empire|Holy Roman]] emperor [[Frederick Barbarossa]] conquered Philippopolis. [[Ivanko (boyar)|Ivanko]] was appointed as the governor of the Byzantine Theme of Philippopolis in 1196, but between 1198 and 1200 separated it from Byzantium in a union with [[Second Bulgarian Empire|Bulgaria]].{{citation needed|date=October 2023}} The [[Latin Empire]] conquered Philippopolis in 1204, and there were two short interregnum periods as the city was twice occupied by [[Kaloyan of Bulgaria]] before his death in 1207.<ref name=pldv>[https://archive.today/20120804175444/http://www.focus-news.net/?id=n819663 Агенция Фокус – Цар Калоян получава корона, скиптър и знаме от кардинал Лъв], посетен на 17 ноември 2007 г.</ref> In 1208, Kaloyan's successor [[Boril of Bulgaria|Boril]] was defeated by the Latins in the [[Battle of Philippopolis (1208)|Battle of Philippopolis]].<ref>Аndreev, J. ''The Bulgarian Khans and Tsars'' (''Balgarskite hanove i tsare'', ''Българските ханове и царе''), Veliko Tarnovo, 1996, p. 180 {{ISBN|954-427-216-X}}.</ref> Under Latin rule, Philippopolis was the capital of the [[Duchy of Philippopolis]], which was governed by [[Renier de Trit]] and later on by Gerard de Strem. The city was possibly at times a vassal of Bulgaria or [[Republic of Venice|Venice]]. [[Ivan Asen II of Bulgaria|Ivan Asen II]] conquered the duchy finally in 1230 but the city had possibly been conquered earlier.<ref>{{cite book |first=John V. A. |last=Fine |title=The Late Medieval Balkans |year=1994 |isbn=978-0-472-08260-5 |url=https://books.google.com/books?id=Hh0Bu8C66TsC |page=125 |publisher=University of Michigan Press |access-date=13 December 2015 |archive-date=30 March 2019 |archive-url=https://web.archive.org/web/20190330024852/https://books.google.com/books?id=Hh0Bu8C66TsC |url-status=live }}</ref> Afterwards, Philippopolis was conquered by Byzantium. According to some information, by 1300 Philippopolis was a possession of [[Theodore Svetoslav]] of Bulgaria. It was conquered from Byzantium by [[George II of Bulgaria|George Terter II]] of Bulgaria in 1322.<ref>Аndreev, J. ''The Bulgarian Khans and Tsars'' (''Balgarskite hanove i tsare'', ''Българските ханове и царе''), Veliko Tarnovo, 1996, p. 253 {{ISBN|954-427-216-X}}.</ref> [[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 price for [[Ivan Alexander of Bulgaria]]'s support in the [[Byzantine civil war of 1341–47]].<ref>Аndreev, J. ''The Bulgarian Khans and Tsars'' (''Balgarskite hanove i tsare'', ''Българските ханове и царе''), Veliko Tarnovo, 1996, p. 272 {{ISBN|954-427-216-X}}.</ref>
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