Timeline

The Second Bulgarian Empire · 1185–1396

From restoration to ruin — two centuries told in five chapters. Each chapter gathers the periods that belong to it, with the years they span, the key events recorded for them, and how much of the realm Tarnovo still held. Follow the spine from the revolt of 1185, through the golden age of Ivan Asen II, to the last resistance at Vidin; open any period for the full article.

I

Before the Empire

1018–1185

Bulgaria under Constantinople — the embers of statehood before the revolt.

No realm — the Bulgarian lands lie under Byzantium.
1018–1185
167 yr

Byzantine Rule

From 1018 to 1185, Byzantium turned Bulgaria into a fully integrated province, governed through themes, garrisons, taxation, and an autonomous archbishopric centered at Ohrid. Under Manuel I the empire briefly regained strength in the Balkans, but frontier pressures, anti-Latin violence, and the Norman capture of Thessaloniki helped create the conditions for the revolt of Ivan Asen and Theodore-Peter, which reopened the way to Bulgarian statehood.

  • 1018Basil II completes the conquest of the old Bulgarian realm and folds its lands into the imperial provincial system.
  • 1019Basil II's triumph in Constantinople ends the Bulgarian patriarchate and establishes an autonomous archbishopric under Ohrid.
  • 1043Theodorokanos destroys a Russian fleet near the Bosphorus, and Katakalon Kekaumenos finishes the survivors near Varna.
  • 1065A raid by the Uzes on the upper Danube prompts Byzantium to reorganize Bulgaria's northern defense zone.
  • 1096–1097The First Crusade crosses the Balkans, forcing the governors of Bulgaria to combine diplomacy with force.
  • 1100Ioannes Komnenos is installed as governor of Bulgaria in Skopje.
  • 1101Ioannes Taronites governs Bulgaria from Skopje.
  • 1171The arrest of Venetian merchants in Constantinople sharpens Byzantine hostility toward the Latins.
  • 1172Manuel I Komnenos presides over a restored Byzantine position in most of the Balkans, with Bulgaria and Macedonia still under imperial administration.
  • 1182Anti-Latin violence in Constantinople reaches its bitterest climax with attacks on foreigners and their property.
  • 1185The Norman capture of Thessaloniki shocks Byzantine authority and becomes a catalyst for the Bulgarian revolt.
  • 1185Ivan Asen and Theodore-Peter appear before Isaac II Angelos at Kypsela and request entry into the Roman army and a village in the Haemus.
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II

The Ascent

1185–1241

Rebellion, restoration, and the climb to imperial power.

12 regions · Ivan Asen II · 1230 — Adrianople · Serres · Prilep
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1185–1197
12 yr

Founding of the Second Empire

Between 1185 and 1197, Theodore and Asen turned a humiliating appeal to Isaac II into a revolt that, with Cuman aid and repeated Byzantine failures, became the restored Bulgarian state centered on Tărnovo. The chapter follows the rise from insurgency to monarchy, the sacral and institutional framing of rule, and the dynastic succession that ended the founding phase with Kaloyan's accession.

  • 1185Theodore and Asen appear before Isaac II at Kypsela, asking for imperial service and a Haemus pronoia; the request is refused and Asen is insulted.
  • 1185The brothers withdraw to the Tărnovo region and raise a declared revolt against Byzantine rule.
  • 1186In Tărnovo they fortify the city, build the church of Saint Demetrius, and proclaim Peter tsar.
  • 1186The uprising spreads north of the Balkan range as rebels seize small fortresses and settlements.
  • 1186Isaac II campaigns in the Balkans and drives the rebels north of the Danube, but cannot secure the mountain strongholds.
  • 1186The brothers recruit Cumans beyond the Danube and return with a stronger mounted force, restoring their position and moving the war into imperial territory.
  • 1187Bulgarian forces raid Lardea, threaten the imperial army near Beroe, and ravage the countryside around Philippopolis.
  • 1187Isaac II reaches Triaditsa, then besieges Lovech for three months without success, although he captures the empress and Kaloyan as hostages.
  • 1189Bulgarian envoys meet Frederick I Barbarossa at Niš and offer help against Isaac II in return for a political settlement.
  • 1190Isaac II marches on Tărnovo, but the imperial army is shattered in the Trevnenski pass.
  • 1192The restored kingdom is consolidated across Moesia, Thrace, Macedonia, and north of the Danube, with Ivan Asen as senior ruler and Peter associated with Preslav.
  • 1195Ivan Asen defeats the Byzantines near Serres.
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1197–1207
10 yr

Kaloyan — Wars with the Crusaders

Kaloyan inherited the restored Bulgarian throne in 1197 and quickly turned the kingdom into a more aggressive Balkan power, fighting Byzantium through alliances, sieges, and opportunistic diplomacy. Between his negotiations with Innocent III, the Latin conquest of Constantinople, and his victories at Adrianople and elsewhere, he brought Bulgaria to the center of regional politics before dying at Thessalonica in 1207.

  • 1197Kaloyan inherits the Bulgarian throne after the violent deaths of Ivan Asen and Peter.
  • 1198He brings Ivanko into cooperation and reaches an understanding with Dobromir Chrysos against Byzantium.
  • 1198–1202A broad war with Byzantium unfolds across Thrace, the Rhodope region, and Macedonia.
  • 1200Ivanko is trapped by deceit and removed from the scene.
  • 1200–1204Kaloyan negotiates with Innocent III for a crown and recognition of the Bulgarian Church.
  • 1201With Cuman aid, Kaloyan captures Konstantsia and then Varna, ending Byzantine control north of the Haimos.
  • 1202Byzantines neutralize Dobromir Chrysos, ending his usefulness as an anti-imperial partner.
  • 1203Kaloyan concludes peace with Byzantium, gaining room to respond to Hungarian pressure on Belgrade and Braničevo.
  • 1204The crusaders sack Constantinople and establish the Latin Empire.
  • 1204Cardinal Leo arrives in Tarnovo and crowns Kaloyan, while the archbishop of Tarnovo is consecrated as primate.
  • 1205Kaloyan sends Bulgarian forces into Thrace and aligns with Greek resistance to Latin rule.
  • 1205Kaloyan defeats the Latins at Adrianople and captures Baldwin of Flanders.
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1207–1218
11 yr

Boril — Internal Struggles

Boril seized the Bulgarian throne in 1207 after Kaloyan’s death, but his reign was immediately undermined by dynastic rivalry, regional defections, and repeated defeats against the Latins and their Balkan allies. He tried to shore up authority through warfare, alliance-making, and the anti-Bogomil council of 1211, yet the kingdom steadily fragmented until John Asen II returned in 1218 and overthrew him.

  • 1207Boril seizes the throne at Tarnovo after Kaloyan’s death and strengthens his claim by marrying Kaloyan’s widow.
  • 1208Boril suppresses most serious internal challengers within the kingdom, though rival Asenids and border magnates remain a threat.
  • 1208Bulgarian forces enter Thrace and clash with Henry near Beroe in an indecisive encounter.
  • 1208Henry defeats Boril near Plovdiv, checking the Bulgarian offensive in Thrace.
  • 1208Alexius Slav enters Henry’s orbit at Stanimaka and receives support, a marriage alliance, and the title of despot.
  • 1209Boril’s troops again prepare to move against imperial territory despite earlier setbacks.
  • 1211Boril convenes the first anti-Bogomil council at Tarnovo and the Synodikon of Orthodoxy is translated into Bulgarian.
  • 1211Henry drives the Bulgarians out of Thrace; Boril supports Strez, whose forces are crushed at Pelagonia by the Thessalonian barons and Michael I Angel.
  • 1211Boril attacks Thessalonica but is defeated by the Lombard barons, aided by Alexius Slav.
  • 1211A rebellion in Vidin prompts Boril to call on Andreas II of Hungary, whose intervention suppresses the revolt and likely costs Boril territory around Belgrade and Braničevo.
  • 1214Hungarian envoys arrange the betrothal of Andreas II’s son Bela IV to Boril’s daughter.
  • 1215Theodorus Doukas emerges as a new force in the southern Balkans, further weakening Boril’s position.
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1218–1241
23 yr
★ Zenith

Ivan Asen II — Golden Age

Ivan Asen II returned from exile in 1218, restored the senior Asen line, and used a blend of dynastic marriage, diplomacy, and war to rebuild Bulgaria’s power. His victory at Klokotnitsa in 1230 and the subsequent reordering of church, coinage, and administration made Tarnovo the center of a major Balkan monarchy, but his death in 1241 left the throne to his infant son Koloman.

  • 1218Ivan Asen returns from exile with Rus’ mercenaries, enters Tărnovo, overthrows Boril, and restores the senior Asen line.
  • 1219Serbia secures peace, and Archbishop Sava obtains recognition of Serbian ecclesiastical autonomy at Nicaea.
  • 1221Ivan Asen marries Andrew II’s daughter with papal approval and Bulgaria recovers Braničevo and Belgrade.
  • 1224Theodore Doukas captures Thessaloniki and expands Epirote power in the Balkans.
  • 1227Theodore Doukas proclaims himself emperor, becoming a major rival in the struggle around Constantinople.
  • 1228Latin barons consider Ivan Asen as a possible regent for Baldwin II and discuss a marriage alliance.
  • 1230At Klokotnitsa on 9 March, Ivan Asen crushes Theodore Doukas’s army and captures Theodore and his boyars.
  • 1230In the aftermath, Ivan Asen installs Bulgarian bishops in Macedonian lands and issues the first Bulgarian gold coin with new royal titulature.
  • 1232–1233Hungarian forces besiege Vidin; Alexander’s relief attempt fails, the fortress holds, and the invaders occupy Severin.
  • 1235The Bulgarian patriarchate is restored and Ivan Asen joins John Vatatzes in an assault on Constantinople.
  • 1237Ivan Asen marries Theodore’s captive daughter, releases Theodore, and the former Epirote ruler returns to Thessaloniki.
  • 1238–1240The destruction of the Cuman state and the fall of Kiev bring Mongol pressure to the frontier; a Bulgarian envoy is well received by Béla IV.
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III

Instability & Recovery

1241–1330

Mongol pressure and contested crowns give way to a fragile recovery.

6 regions · Theodore Svetoslav · 1300 — Tarnovo · Vidin
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1241–1256
15 yr

First Mongol Invasion

After Ivan II Asen’s death, Bulgaria entered a decade of child-rulership, regency, and accelerating territorial decline. The Mongol invasion of 1242 brought devastation and likely tribute, while Nicaea and Hungary exploited Bulgarian weakness; a brief recovery in 1254 was reversed by Theodore II Laskaris, and Michael II Asen’s murder in 1256 pushed the kingdom into crisis.

  • 1241Pope Innocent IV sends a letter to Kaliman I, urging a return to Catholicism.
  • 1241Ivan II Asen dies; the seven-year-old Kaliman I succeeds, and the regency renews ties with Nicaea and concludes a two-year truce with the Latin Empire.
  • 1242The Mongols cross Bulgaria on their return east, ravaging the land, taking booty and prisoners, and likely imposing tribute.
  • 1246Late summer or early September 1246 — Kaliman I dies, reportedly perhaps by poisoning, and Michael II Asen, still a child, becomes tsar.
  • 1246John III Doukas Vatatzes exploits the succession crisis and seizes Serres and other positions in Thrace and Macedonia, while other borderlands slip to the Hungarians.
  • 1247Bulgaria cooperates with Nicaea against the Latin Empire, but only as a junior partner.
  • 1253Michael II Asen issues a charter for Dubrovnik granting broad commercial privileges and waiving customs on trade routes, bridges, and markets.
  • 1254After Vatatzes dies, Bulgarian forces advance into the Rhodope region and recover strongholds including Stanimaka, Perushtitsa, Krichim, Cepina, Ustra, Perperikon, Krivus, Efraim, and the Achrida district apart from Maniak.
  • 1255The Melnik uprising led by Dragota shows local expectations of help from Tarnovo, but no support comes.
  • 1256Theodore II Laskaris campaigns into Europe and drives the Bulgarians back after two costly offensives.
  • 1256Bulgaria and Nicaea conclude a peace that preserves the border but requires the surrender of Cepina.
  • 1256Michael II Asen is murdered by his cousin Kaliman, who briefly seizes the throne and then flees Tarnovo.
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1256–1280
24 yr

Constantine Tikh and Ivaylo's Uprising

From the murder of Michael II Asen in 1256 to the accession of George I Terter in 1280, the chapter traces the collapse of dynastic stability in Bulgaria. Constantine Tikh tried to shore up his rule through marriage, diplomacy, and war, but pressure from Byzantium, Hungary, Nogai's Tatars, and internal fragmentation paved the way for Ivaylo's uprising and a brief Byzantine-backed rival claim.

  • 1256Michael II Asen is murdered by his cousin Kaliman, who seizes the tsar's widow and briefly tries to take power in Tărnovo.
  • 1256Bulgarian forces send a large Cuman contingent into Thrace, defeating Nicene troops and wintering near Dimotika before peace is restored with Nicaea.
  • 1257The boyars of Tărnovo elevate Constantine Tikh as tsar.
  • 1258Constantine takes the name Asen and marries Irene Lascarina, linking himself to the old dynastic network.
  • 1259Hungarian troops under Master Chaka invade the lands beyond the Danube.
  • 1260Constantine's forces are sent into the Severin Banat and are crushed by Master Lawrence; George Akropolitēs arrives in Tărnovo on a diplomatic mission.
  • 1261The Hungarians advance again, cross south of the Danube, and temporarily occupy Vidin.
  • 1262Bulgarian troops raid deep into southeastern Thrace and reach Viza before being stopped by Michael Dukas Tarchaneiotes Glavas.
  • 1263Byzantine forces recover the fortresses of Stanimaka and Philippopolis.
  • 1268Constantine marries Maria Palaiologina Kantakouzene, whose influence later shapes the court and the succession question.
  • 1272Constantine joins the coalition assembled by Charles of Anjou against Byzantium.
  • 1273Darman and Kudelin establish an autonomous lordship in Braničevo, and Nogai's Tatars devastate Bulgaria in a major raid.
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1280–1300
20 yr

Onset of Instability

The chapter traces the collapse of central authority in Bulgaria from 1280 to 1300, as George I Terter survived only by balancing the Horde, Byzantium, and powerful local lords. Repeated Tatar pressure, frontier losses, and dynastic turnover fragmented the kingdom until Theodore Svetoslav seized power in 1300.

  • 1280Ivan III Asen and Ivailo flee to Nogai’s camp; Ivailo is killed there and Ivan III Asen survives through Euphrosyne’s intervention.
  • 1280George I Terter takes the throne in Tărnovo amid civil war and a weakened kingdom.
  • 1281George joins Charles of Anjou’s anti-Byzantine coalition and sends envoys to Italy.
  • 1281At Charles’s prompting, George binds John I Angel to Bulgaria through the planned marriage of John’s daughter to Theodore Svetoslav.
  • 1282The Sicilian Vespers collapse Charles of Anjou’s anti-Byzantine project.
  • 1284Andronicus II makes peace with Bulgaria, recognizes George I Terter, and grants him the title of despot.
  • 1285A devastating Tatar raid forces George to accept Nogai’s overlordship, send Theodore Svetoslav as hostage, and marry his daughter to Chaka.
  • 1291Stephanus Dragutin and Stephanus Uroš II Milutin defeat Darman and Kudelin at Braničevo and attach the province to Dragutin’s lands.
  • 1291Pope Nicholas IV sends the archdeacon Marin to Bulgaria with letters for George I Terter and Patriarch Joakim III, via Queen Helena.
  • 1292Nogai’s men likely replace George I Terter with Smilec, who rules in accommodation with the Byzantines and the Horde.
  • 1292Shishman of Vidin, aided by Tatar troops, invades Serbia, is defeated at Ždrelo, and Vidin is then besieged.
  • 1298After Smilec’s death, the crown passes to the child Ivan IV.
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1300–1330
30 yr

Theodore Svetoslav — Partial Recovery

The chapter follows Theodore Svetoslav’s violent accession in 1300 and his subsequent restoration of Bulgarian authority through internal consolidation, frontier bargaining, and a decisive series of wars against Byzantium. That recovery endured into the reign of Michael Shishman, but the era ended in 1330 with the Bulgarian defeat at Velbuzhd, which reopened dynastic instability.

  • 1300Theodore Svetoslav’s supporters seize Caka in Tarnovo, imprison and strangle him, and execute Patriarch Joachim; Theodore takes the throne in a palace coup.
  • 1301Byzantium sends the purple-born Michael into Bulgaria as a claimant, but he gains no real support and soon becomes irrelevant.
  • 1302Theodore reaches an accommodation with his uncle Eltimir, bringing the Krn region under Tarnovo, and exchanges prisoners with the exiled George I Terter.
  • 1303The sons of Caka, with several thousand horsemen, withdraw into the Vidin territory of Shishman.
  • 1304Theodore opens a campaign against the Hemus fortresses and wins the battle of Skafida against Byzantium.
  • 1304After Skafida, Bulgarian troops advance toward Adrianople and ravage the district.
  • 1305Theodore recovers Mesembria and Anchialos and reasserts Bulgarian control along the southern Black Sea line.
  • 1305He also retakes the Jambol region and overruns Eltimir’s holding after Eltimir shifts sides.
  • 1307Theodore and Byzantium conclude a durable peace, sealed by Theodore’s marriage to Theodora, granddaughter of Andronikos II.
  • 1313Venetian records describe Shishman as ruler of Bulgaria and lord of Vidin, and his son Michael is married to Anna-Neda, daughter of King Milutin.
  • 1322George II Terter succeeds Theodore Svetoslav, while Byzantine pressure again destabilizes the southern frontier and some towns and fortresses drift to Constantinople.
  • 1323After George II’s death, the Bulgarian magnates elect Michael Shishman, uniting the separated parts of Bulgaria.
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IV

The Golden Autumn

1330–1355

A late flourishing of letters and art as the borders fell quiet.

6 regions · Ivan Alexander · 1331 — Tarnovo · Vidin · Nikopol
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1330–1355
25 yr

Ivan Alexander — Cultural Flourishing

Ivan Alexander’s reign began in 1331 with the restoration of native Asenid rule after the collapse of the Serbian-backed regime, and it was immediately tested by revolt, Byzantine pressure, and shifting Balkan politics. He secured the throne through victory and repression, then presided over a period of notable cultural and ecclesiastical flourishing even as regional lordships, heresy, and the Ottoman advance began to weaken the kingdom’s unity.

  • 1331Ivan Alexander took the throne in Tarnovo after the fall of Ivan Stefan's Serbian-backed regime.
  • 1331Belaur of Vidin rebelled against the new king and was defeated with Tatar horsemen.
  • 1331Ivan Alexander defeated Andronikos III at Rusokastro.
  • 1331Stephen Dusan seized power in Serbia after the overthrow and murder of Stephen Decanski.
  • 1332Ivan Stefan and the widow Anna fled from Serbia to Dubrovnik.
  • 1341The Byzantine civil war began, drawing Bulgarian policy into the southern frontier struggle.
  • 1343–1345Momchil established himself as an independent ruler in the Rhodopes.
  • 1350Ivan Alexander and Theodosius of Tarnovo convened an anti-heretical council condemning Bogomils, varlaamites, adamites, and Jews.
  • 1352The Ottomans crossed onto the Balkan Peninsula.
  • 1355Vidin was being shaped as a distinct holding for Ivan Sratsimir.
  • Mid-1340s — Balik broke away in Karvuna, and Dobrotica emerged as the power that gave Dobruja its separate identity.
  • 1340s — Bulgarian troops under Dobrotica and Theodore were sent to aid Anna of Savoy against John Kantakouzenos.
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V

Fragmentation & Fall

1355–1422

The realm splinters and falls to the Ottomans; Vidin resists to the last.

Split into the Tarnovo, Vidin & Dobruja tsardoms — 4 regions, gone by 1396.
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1355–1371
16 yr

Division of the Empire

Between 1355 and 1371, the Bulgarian Empire moved from dynastic continuity toward open fragmentation under pressure from Byzantium, Hungary, regional lords, and the advancing Ottomans. The court, church, and literary culture still projected independence, but military defeats and foreign interventions split the realm into rival centers, ending with the Ottoman victory at the Maritsa.

  • 1355Ivan Alexander renews dynastic diplomacy with Constantinople through a new marriage settlement, sending a Bulgarian princess to the Byzantine capital.
  • 1355The death of Stefan Dušan in December helps throw Serbia into disorder and alter the Balkan balance of power.
  • 1361Patriarch Callistus of Constantinople rebukes the Tarnovo Patriarchate for liturgical and canonical irregularities, and the letter goes unanswered.
  • 1363The Ottomans take Philippopolis and make it a headquarters in Thrace.
  • 1364War breaks out with Byzantium, and John V Palaiologos seizes Anchialos on the Black Sea coast.
  • 1365Hungarian forces cross the Danube near Orșova and capture Vidin on 2 June.
  • 1365Ivan Sracimir and his family are taken captive to Humnik, while a Hungarian administration under Benedikt Himfi is installed in Vidin.
  • 1366John V Palaiologos is detained at Vidin after Ivan Alexander refuses him passage through Bulgarian lands.
  • 1366Amadeus VI of Savoy raids the Black Sea coast, taking Akhtopol, Sozopol, Skafida, Anchialos, and Mesembria and then besieging Varna.
  • 1367John V is released, passes through Kaliakra and Mesembria, and returns to Constantinople as coastal towns shift between Byzantine and Dobruja control.
  • 1368Adrianople falls to the Ottomans.
  • 1371Ivan Alexander dies on 17 February, and the kingdom splits between Ivan Shishman at Tarnovo and Ivan Sracimir at Vidin; Sracimir briefly seizes Sofia.
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1371–1396
25 yr

Fall to Ottoman Power

After Ivan Alexander's death in 1371, the Bulgarian lands fragmented into competing centers while Ottoman victories steadily turned Tarnovo and Vidin into dependent polities. The chapter traces the loss of cities, the imposition of vassalage, and the fall of Tarnovo and Vidin, while showing how church, letters, and charters preserved continuity amid political collapse.

  • 1371Ivan Alexander dies on 17 February and Ivan Shishman succeeds him in Tarnovo as the kingdom is already politically divided.
  • 1371The battle of Maritsa near Černomen destroys the army of John Ugljesa and Vukasin and opens the Balkans to deeper Ottoman advance.
  • 1371Kera Tamara, Ivan Alexander's daughter, is married to Murad I as a pledge of peace and accommodation.
  • 1381Ivan Sratsimir secures Kasinios as metropolitan of Vidin, signaling Vidin's ecclesiastical and political detachment from Tarnovo.
  • 1385The Ottomans capture Sofia, a key strategic and economic hinge in western Bulgaria.
  • 1386Niš falls to the Ottomans, tightening control over the Balkan routes.
  • 1388Ali Pasha's campaign strikes Preslav, Shumen, and Silistra; Ivan Shishman is besieged in Nicopolis and forced into a harsh peace allowing Ottoman garrisons and free troop movement.
  • 1389The battle of Kosovo confirms the new Ottoman order already taking shape in the Balkans.
  • 1392-1393Ivan Shishman's attempt to seek support from Sigismund of Hungary provokes a major Ottoman invasion.
  • 1393Tarnovo is besieged for three months and falls on 17 July; Ivan Shishman is captured and later executed.
  • 1395Ivan Sratsimir sends his son Constantin and Metropolitan Joasaph to Tarnovo, where they obtain the relics of Saint Philothea and transfer them to Vidin.
  • 1396Sigismund's crusade ends in defeat at Nicopolis on 25 September; Vidin is conquered and Ivan Sratsimir is captured, ending independent Bulgarian rule.
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