List of wars involving Serbia in the Middle Ages

• Khan Presian launched an invasion into Serbian territory in 839, which led to a war that lasted for three years, in which the Serbs, led by Price Vlastimir were victorious^[1]

• Boris I sought to avenge the defeat of his father, and in 853 or 854, sends the Bulgar army led by his son, Vladimir-Rasate, to invade the Principality of Serbia^[2]
• The Serbian army, which was led by Mutimir and his two brothers, defeated the invaders, capturing Vladimir and 12 boyars, after which Boris I and Mutimir agreed on peace

Frankish Empire
Byzantine Empire

• Principality of Serbia^[3][4]

• According to On Administering the Empire, "present by [Byzantine] imperial mandate" at the siege were "the Croat and Serb and Zachlumian chiefs and the Terbouniotes and Kanalites and the men of Ragusa and all the cities of Dalmatia", who "were carried over into Lombardy [i.e., Langobardia Minor] by the inhabitants of the city of Ragusa in their own vessels^[5]

• From the Duchy of Croatia, Bran Mutimirović attacks the realm of Petar Gojniković, but suffers defeat and gets captured and blinded^[6]

• Rebellion sponsored by Simeon I of Bulgaria was defeated, resulting in the death of Klonimir and a truce between the Principality of Serbia and the Bulgarian Empire^[7]

• Simeon I decided to deal with Prince Petar Gojniković before advancing further against the Byzantines. An army was dispatched under the command of Theodore Sigritsa and Marmais. The two persuaded Petar Gojniković to meet them, seized him, and sent him to Preslav, where he died in prison^[8]
• Pavle Branovic becomes the new Prince of Serbia^[8]
• Part of Bulgarian–Serbian wars of 917–924

• Zaharija, the exiled son of Pribislav (the eldest of Mutimir's sons), was sent by Romanos I Lekapenos (r. 920–944) to seize the throne. Prince Pavle of Serbia defeated and captured him, handing him over to Symeon, who held him for future use
• Part of Bulgarian–Serbian wars of 917–924

• In 921 Simeon I sent a Bulgarian army headed by Zaharija against the Serbian Principality. The Bulgarian intervention was successful, Pavle was deposed and once again a Bulgarian candidate was placed on the Serbian throne^[9]
• Zaharija becomes the new Prince of Serbia
• Part of Bulgarian–Serbian wars of 917–924

• Zaharija, soon after taking the throne, switched to the Byzantine side, which prompted the retaliatory invasion by Simeon I which resulted in the Bulgarian defeat^[10]
• Part of Bulgarian–Serbian wars of 917–924

• After the previous defeat, a large Bulgarian force was dispatched, accompanied by a new candidate for the Serbian throne, Časlav, The Bulgarians ravaged the countryside and forced Zaharija to flee to the Kingdom of Croatia
• Annexation of Serbia into the Bulgarian Empire^[11]
• End of Bulgarian–Serbian wars of 917–924

• Česlav takes possession of the Serbian Principality and submits to the overlordship of Byzantine emperor Romanos I Lekapenos^[12]

• Mythical, probably unrelated to the 10th century and Časlav
• Victory at Drina
• Defeat at Syrmia

• In 998 Tsar Samuil invaded the Serbian principality of Duklja, which was ruled by Prince Jovan Vladimir
• The Serbs were unable to resist the Bulgarian army, and Jovan Vladimir was captured by Tsar Samuil, however, he married Samuil's daughter and returned to Duklja to rule as a Bulgarian vassal^[13]

• Battle of Bar

• Independence of Duklja from Byzantine rule, Stefan Vojislav defeats Byzantine expeditions against him, and extends his realm on Zachlumia and Travunia

Bulgarian rebels

• Bulgarian rebels chose the son of the Serbian Prince of Duklja Mihailo, Constantine Bodin as their leader, as he was a descendant of the Bulgarian Emperor Samuil, in the autumn of 1072 Constantine Bodin arrived at Prizren where he was proclaimed Emperor of the Bulgarians under the name Peter III
• The Serbian Prince sent 300 soldiers led by Vojvoda Petrilo
• An army under Damianos Dalassenos was immediately sent from Constantinople to help the strategos of the Theme of Bulgaria, Nikephoros Karantenos. In the battle that followed the Byzantine army was completely defeated. Dalassenos and other Byzantine commanders were captured and Skopie was taken by the rebels
• Despite initial successes, rebels were defeated in December of 1072, Constantin Bodin was captured by the Byzantines, which leads to the suppression of the uprising in 1073 by Doux Nikephoros Bryennios^[15]

• King Bodin campaigned in Bosnia and Serbia, then under Byzantine rule, and installed his relative Stephen as knez in Bosnia and his nephews Vukan and Marko as župans in Serbia

• Theme of Dyrrhachium

• King Bodin was captured by the governor of the Theme of Dyrrhachium, John Doukas, but managed to escape in 1091^[16]

• In about 1090, Grand Prince Vukan began raiding Byzantine territory, first in the vicinity of Kosovo
• Byzantines were unable to take steps against Vukan, as they faced a serious threat from the invading Pechenegs^[17]
• Part of Byzantine–Serbian War (1090–1095)

• Alexios I Komnenos sent out an army led by the governor of Durazzo but they suffered defeat
• In 1093 Alexius mobilized a larger army under his leadership and marched on Raska. Vukan immediately sent envoys to the emperor seeking peace and offering homage which Alexius quickly accepted^[18]
• Part of Byzantine–Serbian War (1090–1095)

• Vukan breaks the treaty and begins to expand along the Vardar, obtaining much booty and taking the cities of Vranje, Skopje, and Tetovo^[19]
• Part of Byzantine–Serbian War (1090–1095)

• Battle of Zvečan

• John Komnenos (governor of Dyrrhachium) was defeated by Vukan at Zvečan, which provoked another intervention by Alexios, who now marched towards Serbia with a sizeable army
• Vukan once more sued for peace. Alexios, still pressured by the mounting issues and eager to plug one of many leaks, made simple terms that Vukan accepted^[19]
• End of Byzantine–Serbian War (1090–1095)

• Grand Prince Vukan attacked Byzantium one last time, defeating the army of John Komnenos (governor of Dyrrhachium) once again
• After this victory, Grand Prince Vukan once again reaches a truce with Alexios I Komnenos
• The last mention of Grand Prince Vukan in recorded history^[19]

• Battle of Haram

Grand Principality of Serbia

• As allied Hungarian troops advanced on the Byzantine territory, Serbs had success in their rebellion, capturing the city of Ras
• Hungarian defeat and subsequent peace spelled doom for the Serbian uprising, John II Komnenos suppressed the revolt^[20]

• Battle of Tara (1150)

Kingdom of Hungary

• Serbs rebelled while Emperor Manuel I Komnenos was in Avlona planning an offensive across the Adriatic against Normans
• The rebellion was crushed, Manuel I Komnenos restored Uroš II in 1155 or 1156 and gave Desa the appanage of Dendra near Niš
• Part of a Byzantine–Hungarian War (1149–1155)

• Battle of Sirmium

• Grand Principality of Serbia

• Serbian troops were called upon invasions of Manuel I Komnenos on the Kingdom of Hungary^[21]
• Serbian troops participated in the Battle of Sirmium^[22]

Byzantine Empire

• Stefan Nemanja took advantage of the Hungarian wars to expand his territories and even seized the maritime city of Kotor^[23]
• Stefan Nemanja becomes the new Grand Prince of Serbia

• Battle of Pantina

Byzantine Empire

• While exiled in Byzantium, Tihomir of Serbia asked for military aid, which he got in the form of a mercenary army, however, he was defeated and killed in the battle of Pantina^[24]

• After a short resistance, Stefan Nemanja surrenders to the vastly superior Byzantine army^[25]

• Grand Principality of Serbia

• The Byzantine army, which included Serbian troops sent because of vassal obligations, was defeated by Seljuks^[26]

Grand Principality of Serbia

• Stefan Nemanja joins the Hungarian offensive against Byzantium, scoring a victory and continuing to wage war independently after Béla III finished the campaign^[27]

• Independence of the Grand Principality of Serbia^[28]
• Borders of Serbia expended significantly in the direction of Metohija, Niš, Skopje, and Adriatic^[29]
• Byzantine counteroffensive in 1191 and victory at the Battle of Morava reversed some of Serbian gains, but it was not able to subdue the Grand Principality of Serbia and recover the majority of lost territory^[30]
• Peace deal between Serbia and Byzantium

Byzantine Empire

• Hungarian invasion of the Grand Principality of Serbia prompted the intervention of Isaac II Angelos against the invaders
• Retreat of the Hungarian army
• Stefan Nemanja preserves his throne and state

• Duke Andrew II of Hungary invades Hum, then part of the Grand Principality of Serbia, occupies a part of it temporarily, but then loses it^[33]
• Hum remains a part of the Grand Principality of Serbia

Bulgarian Empire

Kingdom of Hungary

• Status quo ante bellum^[34]
• Vukan, supported by the Kingdom of Hungary, defeats Stefan the First-Crowned and becomes Grand Prince of Serbia, but as Hungarian vassal
• Stefan the First-Crowned exiled to the Bulgarian Empire
• Vukan takes part in successful Hungarian invasion of the Bulgarian Empire in 1202
• Bulgarian emperor Kaloyan defeats Hungarians and successfully invades the Grand Principality of Serbia in 1203^[35]
• Stefan the First-Crowned returns and becomes the Grand Prince of Serbia once again, while Vukan returns to Zeta^[36]

• Strez

• Grand Principality of Serbia successfully invades the western part of the Bulgarian Empire and expands its territory^[37]
• Strez established himself in Prosek, a stronghold from which he began expanding into neighboring Macedonia^[38]

• After successfully invading territories of the Republic of Venice and Arbanon, Michael I Komnenos Doukas invades Zeta
• Although he captures Skadar, his invasion fails and gains get reversed^[39]

• Strez

Latin Empire

• In 1214 the Bulgarian-Latin alliance planned a two-pronged attack on the Grand Principality of Serbia. Troops of Henry of Flanders and Boril of Bulgaria were to advance upon Serbia from the east while Strez invaded from the south
• Serbians try unsuccessful diplomatic action to stop Strez's advance, but he dies shortly after it, leading to the collapse of his forces
• The joint invasion of Serbia fails after the death of Strez^[40]

• In 1237, Coloman of Galicia-Lodomeria attacked Hum
• The northern part, held by a relative of King Vladislav, Toljen II, fell quickly, but Vladislav dispatched an army to regain the region. The crusaders were pushed to the border, and Vladislav pursued them as far as the Cetina River^[42]
• Part of the Bosnian Crusade

• Invasion of Hungary
• Invasion of Serbia
• Invasion of Bulgaria

Kingdom of Hungary

• Defeat of the military alliance led by the Kingdom of Hungary
• Bulgaria enters into vassal relations with the Mongols
• Mongols pass through Serbia burning and looting

Radoslav, Lord of Hum Bulgarian Empire

• Dubrovnik forms an alliance with Tsar Micheal Asen of Bulgaria and Radoslav Andrijić against the Kingdom of Serbia
• Bulgarian army penetrates Serbia as far as Bijelo Polje, but then suddenly retreats^[43]
• No real results from the war^[44]

• Serbian and Epirote armies went into action simultaneously, Michael II Komnenos Doukas rapidly regained most of Albania, most probably including Durazzo, then they went into Macedonia and quickly reoccupied Kastoria and Prilep

• Serbian contingent

Principality of Achaea

• Duchy of Athens
• Duchy of the Archipelago
• Triarchs of Negroponte

Kingdom of Sicily

• Nicaean forces, which included Serbian cavalry units, scored a decisive victory
• It is more probable that rather than a royal army, it may instead have been "some disaffected Serbian nobleman [...] with his own followers" who joined the Nicaeans on his own account, due to the alliance of Uroš I with anti-Nicaean forces^[47]

• The peace treaty established the Serbian tribute, which Dubrovnik had to pay annually to preserve free trade rights in Serbia^[48]

• Serbian invasion devastates Mačva
• Béla IV 's army captures Stefan Uroš I. Their conflict was solved with dynastic marriage

• Battle of Gacko

Kingdom of Hungary

• Stefan Dragutin, with the help of the Kingdom of Hungary, defeats his father, Stefan Uroš I, in the battle of Gacko and becomes the new King of Serbia^[50]

• King of Serbia, Stefan Milutin, joins the campaign of Charles I of Anjou against Byzantium
• The Kingdom of Serbia expends its territory and captures the city of Skopje^[51]

Golden Horde

• Nogai Khan

• Byzantine-Nogai army penetrates Serbia as far as Prizren and Lipljan
• In the battle at river Drim, the Nogai detachment is decisively defeated
• The joint invasion did not affect Serbian military operations as they continued immediately after it^[52]

• Armies of King Stefan Milutin and his brother Stefan Dragutin reach as far as the Aegean Sea^[52]

• Stefan Dragutin doesn't participate in the invasion following the one from 1293, probably to participate in the Hungarian attack on Braničevo^[53]
• Stefan Milutin attacks Byzantium once again, occupying Debar, Poreč, and Kičevo in western Macedonia, and northern Albania^[54]

• Stefan Dragutin

• Darman and Kudelin

• The combined efforts of Hungary and Dragutin in 1285 were unsuccessful in ousting Darman and Kudelin, who quickly struck back by devastating Dragutin’s territories^[55]
• Darman and Kudelin used Cuman and Tatar units, while Stefan Dragutin looked for help from Stefan Milutin to defeat them^[56]
• Darman and Kudelin occupy a large portion of Dragutin's land^[57]

• Stefan Dragutin

• Darman and Kudelin

• Joint forces of Stefan Milutin and Stefan Dragutin defeat Darman and Kudelin and occupy Braničevo^[55]

• Shishman of Vidin

• Shishman of Vidin, an ally of Darman and Kudelin, invades Serbia with his army, which consisted mainly of Tatar soldiers
• Sishman's army penetrates deep into Serbian territory but suffers a decisive defeat at Ždrelo (near Peć)
• The Kingdom of Serbia conducts a successful counteroffensive and captures Vidin^[58]

• Emperor Andronikos II Palaiologos sends an army to retake Macedonia under megas konostaulos Michael Doukas Glabas^[59]
• Even with his extensive military background and the command of a relatively powerful army, Glabas struggled to gain any ground since the Serbs employed guerrilla tactics and avoided direct confrontations, resulting in the failure of the campaign^[60]

• Kotor

Ban of Croatia Zadar

• Armada of Catholic allies attacks Kotor but suffers defeat^[61]
• Part of a greater conflict between the Kingdom of Serbia and the Republic of Ragusa which ended in a peace treaty favorable to Serbia^[62]

• Paul I Šubić of Bribir successfully conquered Hum, and put in its administrative governorship members of the Nelipčić family (Konstantin until 1307, and Izan 1307-1313).^[63] Although his son Mladen II (count of Hum since 1304) was possibly captured, it didn't affect Šubić's territorial control.^[63]

• Paul I Šubić of Bribir, alongside supporting the naval attack on Kotor, penetrates deep into Zeta, reaching Onogošt^[64]
• Today, this invasion is associated with the fighting over Kotor and its surroundings, after which the invaders retreaded from Zeta and the area of Trebinje^[63]

• Kingdom of Serbia

• Repeated raids by the marauding Catalan Company are repulsed by monks of Hilandar monastery with support from King Stefan Milutin^[65]

• Charles Robert

• Frequent raids of the territory of Ugrin Csák, an ally of Charles Robert, by Stefan Dragutin
• Ugrin Csák defeats the army of Stefan Dragutin, but the raids into his territory continue
• Stefan Dragutin makes peace with Charles Robert in Sremska Mitrovica in February of 1314^[66]

• Battle of Gallipoli

• Kingdom of Serbia

• Stefan Milutin sent a detachment of 2000 cavalrymen to aid Byzantium
• Turcopoles are annihilated in the following battle^[67]

• Byzantine Empire

• Originally meant to be a campaign led directly by King Stefan Milutin, however, he got preoccupied with the war against Mladen II Šubić in the west
• Veliki vojvoda Novak Grebostrek takes command of the campaign and leads it against Aydinids, scoring victories
• Despite not changing the dire situation of the Byzantine Empire, this expedition is celebrated by both Greek and Serbian sources^[68]

Realm of Stefan Dragutin

• In 1312 or 1313, brothers Stefan Milutin and Stefan Dragutin planned a re-conquest offensive against the Šubić family in Hum, but it is not clear what are the results of this war and "possibly never happened".^[63]

• As part of Hungarian-Italian initiative against the Serbian king, Mladen II Šubić attacks eastern Hum, Trebinje and Konavle with significant success.^[63]
• However, a year later the tide changes, and Mladen's brother, Grgur Šubić, gets captured along with two other nobles, prompting peace negotiations, and the Šubić's agree to restore eastern Hum to Milutin.^[63]

• Muzaka family lead the revolt^[69]
• Pope John XXII and Philip I of Taranto support the revolt

• Revolt crashed by Stefan Milutin^[70]

• After the death of Stefan Dragutin, the Kingdom of Serbia occupied most of his realm, which the Kingdom of Hungary considered to be theirs^[71]
• Provoked by this action, Charles Robert, with the support of Pope John XXII, tries to assemble a Catholic coalition against Stefan Milutin, but this diplomatic action fails
• Warfare between the two kingdoms results in Hungarian victory in Mačva, but, Serbia managed to keep Braničevo and prevent further advances into its territory^[72]

• Branivojevići, a local noble family or agents of King Milutin, take control of Hum, expending their influence from the eastern to the western part of it
• Although it is unclear if they also conquered Ston and Pelješac during or after the rule of Mladen II, they did participate in his downfall

• Branivojević

Republic of Ragusa

• Joint Bosnian-Ragusan action against the Branivojević noble family, who were a semi-independent Serbian noble family, and the unpreparedness of Stefan Dečanski to help his vassals, led to the loss of Hum^[73]
• Bosnian renewed invasion of the Kingdom of Serbia in 1328/1329 was defeated by Stefan Dušan, which is the first recorded conflict of the future Emperor of Serbia^[74]
• Despite some reversal of Bosnian gains^[74] Ban Stephen II Kotromanić keeps most of Hum

• Kotor

• After occupying the territories of Branivojević, relations between Serbia and Ragusa were tense
• A new war between the two states starts in the fall of 1327 and lasts till the fall of 1328, resulting in the Serbian reconquest of Ston^[75]

• Battle of Velbazhd

• Western mercenaries

• Cumans
• Tatars
• Jasz
• Wallachia

Byzantine Empire

• Emperor Andronikos III and Emperor Michael Asen III settled an anti-Serbian peace treaty on the 13th of May 1327^[76]
• The joint invasion of the Kingdom of Serbia starts in July of 1330, with the Byzantine advance from the South and the Bulgarian advance from the East^[77][78]
• Bulgarian forces are decisively defeated at the battle of Velbazhd^[79]
• Bulgarian defeat leads to the collapse of the coalition against Serbia^[80]

• First conquest of Byzantium conducted by Stefan Dušan
• Although limited in scope compared to the later campaigns, Serbians occupied Strumica and expanded their territory South^[81]

• Dušan began campaigning against the Byzantine Empire in late 1333, when Syrgiannes, a leading Byzantine general, switched sides^[82]
• After the significant success of the campaign, it comes to a halt after Syrgiannes is murdered by Byzantine conspirators
• Peace deal between King Stefan Dušan and Emperor Andronikos III Palaiologos from 1334 confirms most of the Serbian conquest^[83]

• Banate of Bosnia

• While Stefan Dušan was campaigning in Macedonia, Charles I, supported by Stephan II, launched an invasion of the northern territory of the Kingdom of Serbia^[84]
• With the news of Stefan Dušan's return, the Hungarian army rapidly retreats with possible high casualties while trying to cross the river Sava^[85]

• Capetian House of Anjou

• Albanian defense collapsed and city of Durazzo fell^[86]
• The Kingdom of Serbia had "limited success" in central Albania^[84]
• Angevin prince, Louis of Durazzo, gained successes while fighting against Serbs^[87]

• John VI Kantakouzenos

• Intervention of King Stefan Dušan on behalf of pretender John VI Kantakouzenos in his war against regent Anna of Savoy
• Intervention in the civil war turns into conquest of south Macedonia, with Edessa, Kastoria, and Florina falling under the Kingdom of Serbia^[88]
• Part of the Byzantine civil war of 1341–1347

• Capetian House of Anjou

• Stefan Dušan launches a great invasion of Albania^[89]
• Swift and methodological conquest of major Albanian strongholds
• Although the fate of Durazzo is unknown, the whole of Albania is occupied by the Kingdom of Serbia by 1346

• King Stefan Dušan sends his elite units under his general Preljub in order to fight against the Turks
• Superior tactical awareness and mobility of Turks bring them victory
• Possible short halt of offensive actions by King Stefan Dušan^[90]

• John VI Kantakouzenos
• Emirate of Aydin

• Stefan Dušan turns hostile against John VI Kantakouzenos and concludes a formal alliance with the regency^[91]
• The Kingdom of Serbia attacks Byzantine territory, capturing Serres after a long siege, while Kantakouzenos-Turkish forces fail to drive the invaders out, prioritizing attacking regent Anna of Savoy^[88]
• After these conquests, Stefan Dušan becomes Emperor of the Serbs
• Part of the Byzantine civil war of 1341–1347

• John VI Kantakouzenos becomes the new Byzantine emperor
• Black Death devastates Greek territories, leaving them vulnerable
• Emperor Stefan Dušan launches an invasion of the Byzantine Empire and conquers Epirus, Aetolia, Acarnania, and Thessaly^[92]

• Serbian Empire attacks the region of Hum, which Banate of Bosnia occupied in 1326, and achieves significant success
• However, Emperor Stefan Dušan turns his army south on the news that John VI Kantakouzenos has launched invasion of the newly-acquired Serbian land
• Only small garrisons left to defend Hum, which Stjepan II Kotromanić had no problem defeating^[93]

• Ottoman beylik^[94]

• Byzantine Empire, with additional Turkish troops, invades the Serbian Empire, achieving significant success, but the siege of Servia fails^[95]
• Serbian counteroffensive reverses the gains of the Byzantines^[96]

• Battle of Demotika

• John V Palaiologos
• Bulgarian Empire

• Ottoman beylik

• Serbian intervention in the Byzantine civil war of 1352–1357 on the behalf of John V Palaiologos
• The joint army of Serbians, Bulgarians, and Greeks was defeated by more numerous Ottomans in the Battle of Demotika^[97]
• The battle was the first major battle of the Ottomans on European soil

• War can be classified as a crusade against schismatics^[98]
• The initial invasion of the northern parts of the Serbian Empire was successful, which prompted Emperor Stefan Dušan to start negotiations with Pope Innocent VI on recognizing papal supremacy, although it is questionable how sincere this attempt was^[99]
• Despite initial successes, the Hungarian invasion was defeated while the Serbian counteroffensive might have captured additional territory from the Kingdom of Hungary

• Nikephoros II Orsini swiftly captures Thessaly and Epirus after the death of Stefan Dušan and Preljub
• However, he does not return the territory to the Byzantine Empire, but reestablishes the Despotate of Epirus^[100]

• Byzantine army, led by two powerful magnates, reoccupied territories on the southeastern border of the Serbian Empire

• Ottoman beylik

• Matthew Kantakouzenos, with an army primarily consisting of Turkish mercenaries, attacked Serres
• The commander of the Turkish troops was killed early in the battle of Serres, which spelled doom for the forces of Matthew Kantakouzenos, who gets captured after the battle^[102]

• Republic of Venice

• Powerful magnate John Komnenos Asen establishes himself as an independent ruler
• His might will be greatly reduced over time, leading to the collapse of his realm^[103]

• Greek and Albanian supporters

• Simeon Uroš, half-brother of Stefan Dušan, proclaims himself as the new Serbian Emperor and gathers a sizable army consisting of Greek and Albanian troops^[104]
• Simeon Uroš occupies a large part of the Despotate of Epirus
• Stefan Uroš V, who is supported by most of the Serbian nobility, defeats the pretender's army near Skadar, and Stefan Uroš is never again a threat to his rule^[100]

• After the death of Nikephoros II Orsini in the Battle of Achelous Simeon Uroš reestablishes the Serbian control of Thessaly and Epirus, but as an independent ruler^[105]

• Rastislalić noble family

• The Kingdom of Hungary interferes in the fighting of northern Serbian nobles, installing Rastislalić as their vassals, who soon after became independent
• This intervention soon became the full-scale invasion of the Serbian Empire, headed personally by Louis I of Hungary
• Uroš V meets invaders on the battlefield, but suffers defeat
• Serbs turn to guerilla warfare in the hills, which Hungarians had no answer for, so their army retreats^[106]

• Vojislav Vojinović

• This conflict could be seen as a continuation of the Hungarian-Serbian War of 1359, as the Republic of Ragusa became a subject of the Kingdom of Hungary after the Treaty of Zadar^[107]
• Vojislav Vojinović, with the approval of Emperor Uroš V, invades the territory of the Republic of Ragusa and devastates it
• Republic of Ragusa pays tribute to Vojislav Vojinović^[108]

• Vojislav Vojinović
• Kotor

• Balšići
• Budva

• Beginning of the collapse of the central power in the Serbian part of the Serbian Empire as Balšić and the town of Budva openly sided with the Republic of Ragusa^[109]
• War began with military attacks and devastation of inland territories of Ragusa, which responded by naval blockade of Kotor
• Still, Ragusa was suffering losses, however, the tide changes when Balšiči and Budva entered the war on their side
• Peace concluded between Ragusa and the Serbian Empire, which proved that the war ended inconclusively^[110]

• Matarangos

• Đurađ I Balšić, together with his Matarangos allies, declare war against Thopia, noble family which controlled northern Albania
• Đurađ I Balšić gets captured by Karl Thopia and gets held until 1366, when Republic of Ragusa mediated peace and procured his release^[111]

• Thomas Preljubović

• As a part of Epirus is overrun by Albanians, the city of Ioannina asked Simeon Uroš for protection, and he sends Thomas Preljubović as a new Despot of Epirus, establishing Serbian administration of the city of Ioannina in 1368^[112]
• Peter Losha leads Albanians in the long siege of Ioannina, which ends in a peace and marriage agreement

• New invasion of the territory of Karl Thopia by Balšić noble family is successful as Ulcinj is incorporated in their territory^[113]

Ottoman Empire

• Uglješa Mrnjavčević, the despot of feudal state centered in Serres, significantly increased his holdings
• Frequent fighting with raiding Turks, in which despot scores victories^[114]
• It is most probable that those victories were against smaller raiding parties, which motivates the Despot Uglješa Mrnjavčević to deal with a Turkish threat^[115]

• Battle of Maritsa

• Vukašin of Serbia

Uglješa Mrnjavčević

• The diplomatic action of Uglješa Mrnjavčević to form a grand Christian alliance to drive the Turks out of the Balkans fails, with only his brother answering the call
• The army of the two brothers was large, but nowhere near the claim of 60 000 that was reported by later sources^[116]
• Serbian army was decisively defeated and the two brothers died in the battle, leading to the loss of southern Serbian lands
• Collapse of the Serbian Empire^[117]

• Thomas Preljubović

• After the plague that killed Peter Losha, Gjin Bua Shpata leads new attacks against Ioannina, raiding its countryside
• Peace and marriage agreement between the warring parties^[112]

• Thomas Preljubović

• Malakasioi

• Albanian chieftain named Gjin Phrates led an army of Malakassaioi in an attack on the city on September 14, 1377, however, he was defeated and triumphantly paraded around the streets while captured soldiers were sold into slavery
• First victory of Thomas Preljubović over Albanians^[118]

• Thomas Preljubović

Despotate of Arta

• Gjin Bua Shpata

• Juan Fernández de Heredia

• Serbian-Albanian alliance defeats the Frankish forces led by Juan Fernández de Heredia, who himself gets captured and sold
• Albanians recapture the territory taken by the Knights Hospitaller^[119]

• Thomas Preljubović

• Malakasioi
• Local Bulgarians and Vlachs

• Malakasioi amphibious and land attack on Ioannina, although planned well with the help of a local traitor, was defeated, and the captives were brutally treated by the Despot Thomas Preljubović
• After this siege, the attack of Gjin Bua Shpata on Ioannina was defeated too, Thomas Preljubović brutalized prisoners
• Thomas Preljubović goes down in history as the Albanitoktonos, the slayer of Albanians^[120]

• Battle of Dubravnica

• The incursion of Turkish troops into the Principality of Moravian Serbia, probably after military operations in Bulgaria
• Serbian forces of Prince Lazar, led by commanders Vitomir and Crep defeated the invading Ottoman Turks of Sultan Murad I in the battle of Dubravnica^[121]

• Thomas Preljubović

Ottoman Empire

• Malakasioi
• Local Bulgarians and Vlachs

• In 1381, Thomas II Preljubović, accompanied by Ottoman auxiliary forces, launched an invasion of the Despotate of Arta
• He is successful and managed to expand his control in Dryinopolis, Velas, Boursina, Krezounista, Dragomi and Vagenetia and most of the land previously under the control of the Malakasioi tribe^[122]

• Prince Lazar established himself as the most powerful lord after the fall of the Serbian Empire, and expanded his territory north to the Danube river, while still being the vassal of King Louis I of Hungary
• When King Louis dies, Prince Lazar declares independence and attacks Golubac and Belgrade, and crosses the Sava river
• Although attacks on Golubac and Belgrade fail, Prince Lazar becomes an independent ruler

• Battle of Savra

• Ottoman Empire

• Balša II successfully invades territories of Karl Thopia, managing to conquer Durazzo
• However, with the help of the Turkish army, Balša II is defeated and killed in the battle of Savra, and Karl Thopia restores control of the lost territory^[124]
• Loss of the Albanian territories held by Balšići

• Battle of Pločnik

• Large-scale invasion of the realm of Prince Lazar led personally by Murad I
• Ottomans conquer Niš, an important strategic town and logistical center, which enables their future conflicts
• However, Ottoman invasion is stopped at Pločnik, Prince Lazar strengthens defenses of his realm
• Prelude of the Battle of Kosovo

• Battle of Kosovo

• Kingdom of Bosnia
• Realm of Vuk Branković

• Beylik of Isfendiyar

• The Ottoman invasion led personally by Murad I met strong resistance in the form of a Christian coalition led by Prince Lazar, leading to one of the largest battles of the late medieval times^[126]
• Ottomans had a significant numerical advantage and more reserves that were not called to participate in the invasion, while the entirety of Serbian forces were called upon^[127]
• Both Murad I and Prince Lazar are killed during the battle, and the bulk of both armies is destroyed
• Bayezid I, son of Murad I, upon hearing of his father's death, murders his brother, Yakub Çelebi, securing the title of Sultan
• Remaining Ottomans retreat from Serbian territory, however, less numerous Serbian forces are significantly depleted

• Ottoman Empire

• Sigismund of Luxembourg invades Serbian territory right after the Battle of Kosovo, and depleted Serb are not able to put up effective resistance
• Caught between the two expansionist powers, Prince Stefan Lazarević had to act diplomatically to save his state
• The State Assembly with the support of Serbian Patriarch Spyridon (1379–1389), decided on the conclusion of peace and acceptance of the supremacy of Sultan Bayezid I
• Serbians, with the help of Ottoman troops, pushed Hungarians out, recaptured the lost territory, and continued raids into the Kingdom of Hungary
• The Kingdom of Hungary temporarily lost Golubac to Turks twice, but in 1382, Sigismund of Luxembourg kicked the Turks out and conducted a raid deep into Serbian territory

Principality of Zeta

• Serbian lands that were not a part of the realm of Stefan Lazarević were a target of Turkish conquest
• Both Vuk Branković and Đurađ II Balšić suffer significant territorial losses and become vassals of the Ottoman Empire

• Ottoman Empire

• Konstantin Balšić, as an Ottoman vassal, invades and captures Dagnum and establishes supremacy over local Albanian nobles^[130]

• Republic of Venice

• Konstantin Balšić

• Đurađ II Balšić breaks his Ottoman vassalage and successfully invades northern Albania while Ottomans are busy with their campaign in Wallachia
• Principality of Zeta conquers Skadar and other territories, defeating Konstantin Balšić in the process^[130]
• However, Đurađ II is aware that he can not stop further Turkish invasions, so he offers the newly acquired territory to the Republic of Venice

• Battle of Rovine

• Stefan Lazarević
• Marko Mrnjavčević
• Konstantin Dejanović
• Konstantin Balšić

Kingdom of Hungary

• Great invasion force led personally by Bayezid I, which included many of his Serbian vassals, was defeated by Wallachian forcces led by Mircea I in the Battle of Rovine
• Many of Ottoman vassals died in this battle, and Bayezid I annexed their territories after retreating from Wallachia
• Sigismund of Luxembourg successfully invades Ottoman territories after the battle, giving him hope for a future crusade against the Ottoman Empire

• Ottomans capture the majority of territory held by Vuk Branković

• Battle of Nicopolis

• Moravian Serbia

Kingdom of Hungary

• Great crusader army crosses the Danube river and captures Vidin
• Bayezid I found himself in a predicament, but bad organization of the Crusade and Western unfamiliarity with the Turkish battle tactics worked in his favor
• In the Battle of Nicopolis Crusaders suffered a decisive defeat, with the Serbian contingent of Stefan Lazarević, consisting of heavily armored cavalry, being the decisive factor
• Crusaders are driven back, and Ottomans, together with the troops of Stefan Lazarević, conduct a large-scale raiding operation in the Kingdom of Hungary
• Vuk Branković is captured and the majority of his territory is given to Stefan Lazarević

• Battle of Ankara

• Moravian Serbia
• District of Branković
• Other Ottoman vassals

• Aq Qoyunlu
• Germiyanids

• One of the greatest battles of the Middle Ages with high consequences for the Ottoman state^[134]
• Although Timur was more interested in expanding into Mesopotamia and Egypt, Bayezid's demand for tribute offended this mighty ruler, moving him to start a campaign against Ottomans
• The battle was catastrophic for Ottomans, however, a contingent of Serbian knights fought heroically, even when surrounded, defeating several Mongol assaults
• Serbian knights break off the encirclement and return from the battlefield
• While returning, Stefan Lazarević visits Constantinople, where John VII Palaiologos, who was ruling the Byzantine Empire in the absence of Manuel II Palaiologos, awards him with the prestigious title of Despot
• Beginning of the Serbian Despotate^[135]