Andronikos III Palaiologos, commonly Latinized as Andronicus III Palaeologus, was the Byzantine emperor from 1328 to 1341. He was the son of Michael IX Palaiologos and Rita of Armenia. He was proclaimed co-emperor in his youth, before 1313, and in April 1321 he rebelled against his grandfather, Andronikos II Palaiologos. He was formally crowned co-emperor in February 1325, before ousting his grandfather outright and becoming sole emperor on 24 May 1328.
John V Palaiologos or Palaeologus was Byzantine emperor from 1341 to 1391, with interruptions. His long reign was marked by constant civil war, the spread of the Black Death and several military defeats to the Ottoman Turks, who rose as the dominant power of the region.
Stefan Uroš IV Dušan, known as Dušan the Mighty, was the king of Serbia from 8 September 1331 and tsar and autocrat of the Serbs, Greeks, Albanians and Bulgarians from 16 April 1346 until his death in 1355.
The Serbian Empire was a medieval Serbian state that emerged from the Kingdom of Serbia. It was established in 1346 by Dušan the Mighty, who significantly expanded the state.
Ivan Alexander, also sometimes Anglicized as John Alexander, ruled as Emperor (Tsar) of Bulgaria from 1331 to 1371, during the Second Bulgarian Empire. The date of his birth is unknown. He died on 17 February 1371. The long reign of Ivan Alexander is considered a transitional period in Bulgarian medieval history. Ivan Alexander began his rule by dealing with internal problems and external threats from Bulgaria's neighbours, the Byzantine Empire and Serbia, as well as leading his empire into a period of economic recovery and cultural and religious renaissance.
Anna of Savoy, born Giovanna (1306–1365), was a Byzantine Empress consort, as the second spouse of Andronikos III Palaiologos. She served as regent, with the titles augusta and autokratorissa, during the minority of her son John V Palaiologos from 1341 until 1347. In Byzantium, she was known as Anna Palaiologina, owing to her marriage to Andronikos.
Irene Asanina, was the empress consort of John VI Kantakouzenos of the Byzantine Empire. She is known to have participated in military issues in a degree uncommon for a Byzantine empress. She commanded the garrison of Didymoteicho during the Byzantine civil war of 1341–1347, and organized the defense of Constantinople against the Genoese in 1348, and the forces of John V in 1353.
The Battle of Stephaniana was a small-scale battle between the forces of the Medieval Serbian Kingdom and the Emirate of Aydin, allies of Byzantine emperor John VI Kantakouzenos. It was the first battle between the Serbs and Turks, as an earlier battle in Gallipoli was fought between troops sent by King Milutin and Turcopole Halil Pasha (1312).
The Byzantine civil war of 1341–1347, sometimes referred to as the Second Palaiologan Civil War, was a conflict that broke out in the Byzantine Empire after the death of Andronikos III Palaiologos over the guardianship of his nine-year-old son and heir, John V Palaiologos. It pitted on the one hand Andronikos III's chief minister, John VI Kantakouzenos, and on the other a regency headed by the Empress-Dowager Anna of Savoy, the Patriarch of Constantinople John XIV Kalekas, and the megas doux Alexios Apokaukos. The war polarized Byzantine society along class lines, with the aristocracy backing Kantakouzenos and the lower and middle classes supporting the regency. To a lesser extent, the conflict acquired religious overtones; Byzantium was embroiled in the Hesychast controversy, and adherence to the mystical doctrine of Hesychasm was often equated with support for Kantakouzenos.
Dejan was a magnate who served Serbian Emperor Stefan Dušan as sevastokrator, and Emperor Uroš V as despot. He was married to Emperor Dušan's sister Teodora, and possessed a large province in the Kumanovo region, east of Skopska Crna Gora. It initially included the old župe (counties) of Žegligovo and Preševo. Uroš V later gave Dejan the Upper Struma river with Velbužd (Kyustendil). Dejan rebuilt the Zemen Monastery, one of Dejan's endowments, among others, as he also reconstructed several church buildings throughout his province.
The Kingdom of Serbia, or the Serbian Kingdom, was a medieval Serbian state that existed from 1217 to 1346 and was ruled by the Nemanjić dynasty. The Grand Principality of Serbia was elevated with the regal coronation of Stefan Nemanjić as king, after the reunification of Serbian lands. In 1219, Serbian Orthodox Church was reorganized as an autocephalous archbishopric, headed by Saint Sava. The kingdom was proclaimed an empire in 1346, but kingship was not abolished as an institution, since the title of a king was used as an official designation for a co-ruler of the emperor.
Radoslav Hlapen was a Serbian magnate who served Serbian Emperor Stefan Dušan and Stefan Uroš V as vojvoda. He took part in the conquest of Byzantine lands, and was given a region north of Thessaly to govern in the early 1350s.
Vojihna or Vojin of Drama, was a Serbian nobleman that rose through the ranks and became one of the most acclaimed military commanders (voivode) and dukes of Stephen Uroš IV Dušan of Serbia during the Serbian Kingdom and Empire (1331–71), he was titled Caesar, hence, he is mostly known as Caesar Vojihna. He held the region of Drama.
The fall of the Serbian Empire was a decades-long process in the late 14th century. Following the death of the childless Emperor Stefan Uroš V in 1371, the Empire was left without an heir and the magnates, velikaši, obtained the rule of its provinces and districts, continuing their offices as independent with titles such as gospodin, and despot, given to them during the Empire. This period is known as the dissolution or the beginning of the fall of the Serbian Empire.
The Byzantine civil war of 1352–1357 was an armed conflict resulting from and following the Byzantine civil war of 1341–1347. The war pitted Byzantine emperor John V Palaiologos against John VI Kantakouzenos and his eldest son Matthew Kantakouzenos. John V emerged victorious as the sole emperor of the Byzantine Empire, but the destruction brought about by the civil war left the Byzantine state in ruins.
The House of Dejanović or House of Dragaš originates from a medieval noble family that served the Serbian Empire of Dušan the Mighty and Uroš the Weak, and during the fall of the Serbian Empire, after the Battle of Maritsa (1371), it became an Ottoman vassal. The family was one of the most prominent during these periods. The family held a region roughly centered where the borders of Serbia, Bulgaria and North Macedonia meet. The last two Byzantine Emperors were maternal descendants of the house.
Nikola Buća was a Serbian nobleman, merchant from Kotor, and protovestijar in the service of King Stephen Uroš III Dečanski of Serbia and Emperor Stephen Dušan the Mighty.
Gradislav Borilović was a Serbian magnate in the service of Stefan Uroš III Dečanski and Stefan Dušan, having the titles of vojvoda (general), kaznac, and tepčija. Gradislav led the Serbian army that fought the Ottoman emirate at the Battle of Demotika in October 1352. The battle was fought between the allies of the two rival Byzantine Emperors, John V Palaiologos and John VI Kantakouzenos, and it was the first major battle of the Ottomans on European soil, which ended in a Serbian defeat. Greek sources spoke of Gradislav as "truly one of the most respectable among the Serbs".
The Serbian civil war of 1331 broke out following King Stefan Uroš III's decision not to continue campaigning against the Byzantine Empire when he had the chance following the victory at the Battle of Velbazhd against Bulgaria, alienating much of the nobility, which became divided supporting either Uroš III or his son, Stefan Dušan.
The Didymoteicho Fortress or Castle, is an ancient and medieval hilltop citadel complex in the town of Didymoteicho, Thrace, Greece. It has been an important landmark since ancient times due to the strong fortification surrounding it. The castle is accompanied by several myths, one of the most famous is that of the Forty Arches, and is where Charles XII, King of Sweden, is said to have been imprisoned by the Turks.
John V Palaiologos 
Serbian Empire 
Second Bulgarian Empire 
Ottoman Beylik