Wins and Losses of the Second Bulgarian Empire, 1185–1396

Battles, sieges, raids and campaigns of the Second Bulgarian Empire from 1185 to 1396. Of the 151 with a known outcome: 69 won, 7 drawn and 75 lost.

By opponent

By opponent
OpponentWonDrawnLostWon %
Byzantium3732458%
Ottomans502020%
Latin Empire1111050%
Nicaea51545%
Tatars30633%
Hungary21429%
Serbia21333%
Amadeus of Savoy20167%
Turks of Aydin10150%
Epirus100100%
Venice0010%
Total6977546%

By ruler

Every engagement

  1. 1185

    Attempt on Preslav

    Siege · against Byzantium · Peter IV (Theodore-Peter)

    Peter attacks the old capital, but its walls hold.

    Jr., p. 31

    Lost
  2. 1186

    Night battle against John Kantakouzenos

    Battle · against Byzantium · Ivan Asen I

    The blinded commander underrates Asen and is routed in a night attack in the mountains.

    Bozhilov & Gyuzelev, p. 626 · Jr., p. 32

    Won
  3. 1186

    Isaac II's first campaign

    Campaign · against Byzantium · Ivan Asen I

    The emperor drives the brothers across the Danube; they return in the autumn with Cumans.

    Jr., p. 33

    Lost
  4. ~1186

    Battle near Lardea

    Battle · against Byzantium · Ivan Asen I

    Asen all but routs the army led by the emperor himself.

    Bozhilov & Gyuzelev, p. 626

    Won
  5. ~1186

    Success near Beroe and raid toward Philippopolis

    Raid · against Byzantium · Ivan Asen I

    Bozhilov & Gyuzelev, p. 626

    Won
  6. 1187

    The Cumans at Adrianople

    September · Battle · against Byzantium · Ivan Asen I

    Isaac narrowly beats the Cumans besieging the city after their feigned flight.

    Jr., p. 33

    Lost
  7. 1188

    Siege of Lovech

    Siege · against Byzantium · Ivan Asen I

    Isaac's failed campaign ends in a treaty; Asen's wife is left as a hostage.

    Bozhilov & Gyuzelev, p. 627 · Jr., p. 33 · Bozhilov, p. 35

    Won
  8. 1190

    Siege of Tarnovo

    Siege · against Byzantium · Ivan Asen I

    Isaac II lifts the siege on a rumour of an attack from behind.

    Angelov & Cholpanov, p. 100 · Bozhilov & Gyuzelev, p. 629 · Jr., p. 43

    Won
  9. 1190

    Tryavna Pass

    Battle · against Byzantium · Ivan Asen I

    The retreating Byzantine army is cut down in the pass; the emperor barely escapes.

    Angelov & Cholpanov, p. 100 · Bozhilov & Gyuzelev, p. 629 · Jr., p. 43

    Won
  10. 1191

    Capture of Varna and Anchialos

    Campaign · against Byzantium · Ivan Asen I

    Dated 1190, 1191 or 1192; the Byzantines soon take both towns back.

    Angelov & Cholpanov, p. 104 · Bozhilov & Gyuzelev, p. 630 · Bozhilov, p. 32

    Won
  11. ~1191

    Sredets, Niš and Stobi

    Campaign · against Byzantium · Ivan Asen I

    Asen takes and razes Sredets, takes Stobi and reaches Niš.

    Angelov & Cholpanov, p. 104 · Bozhilov & Gyuzelev, p. 630

    Won
  12. 1193

    Repulsed at Philippopolis and Beroe

    Battle · against Byzantium · Ivan Asen I

    Constantine Angelos drives off the Cumans at Philippopolis and the Vlachs near Beroe.

    Angelov & Cholpanov, p. 104 · Jr., p. 44

    Lost
  13. 1194

    Arcadiopolis

    Battle · against Byzantium · Ivan Asen I

    The armies of Alexios Gidos and Basil Vatatzes are destroyed; Vatatzes is killed.

    Angelov & Cholpanov, p. 105 · Bozhilov & Gyuzelev, p. 630 · Jr., p. 45

    Won
  14. 1195

    Serres: Alexios Aspietes captured

    Battle · against Byzantium · Ivan Asen I

    Asen surprises the camp before Serres and takes its general prisoner; Melnik and Strumica fall too.

    Angelov & Cholpanov, p. 105 · Bozhilov & Gyuzelev, p. 632 · Jr., p. 46

    Won
  15. 1196

    Ambush at Amphipolis

    Battle · against Byzantium · Ivan Asen I

    The sebastokrator Isaac Komnenos is captured. Fine dates the capture 1195, the military history 1196.

    Angelov & Cholpanov, p. 105 · Bozhilov & Gyuzelev, p. 632 · Jr., p. 46

    Won
  16. 1196

    Peter besieges Ivanko in Tarnovo

    Siege · Peter IV (Theodore-Peter)

    After Asen's murder Ivanko holds Tarnovo, then flees to the Byzantines.

    Bozhilov & Gyuzelev, p. 633 · Jr., p. 46

    Civil war
  17. ~1197

    Siege of Strumica

    Siege · against Byzantium · Dobromir Chrysos

    Alexios III besieges Chrysos for two months without success.

    Jr., p. 47

    Won
  18. 1198

    Krichim

    Siege · against Byzantium · Ivanko

    The Byzantines take Ivanko's fortress.

    Angelov & Cholpanov, p. 106

    Lost
  19. 1198

    Ambush at Batkun

    Battle · against Byzantium · Ivanko

    Manuel Kamytzes is captured.

    Angelov & Cholpanov, p. 107 · Jr., p. 48

    Won
  20. 1199

    Batrachokastron

    Battle · against Byzantium · Ivanko

    A heavy defeat for the Byzantine army; soon after, Ivanko is seized by a trick.

    Bozhilov & Gyuzelev, p. 640 · Bozhilov, p. 45

    Won
  21. 1199

    Raid into Eastern Thrace

    Raid · against Byzantium · Kaloyan

    The Vize garrison beats the raiders, and is then beaten in turn by the Cumans.

    Angelov & Cholpanov, p. 108

    Drawn
  22. 1199

    Siege of Prosek

    Siege · against Byzantium · Dobromir Chrysos

    Chrysos' stronghold above the Vardar holds.

    Angelov & Cholpanov, p. 109 · Jr., p. 50

    Won
  23. 1200

    Stenimachos

    Siege · against Byzantium · Ivanko

    Alexios III takes Stenimachos, and Ivanko is captured on false oaths.

    Angelov & Cholpanov, p. 107 · Bozhilov, p. 45

    Lost
  24. 1201

    Raid to the walls of Constantinople

    Raid · against Byzantium · Kaloyan

    Angelov & Cholpanov, p. 111

    Won
  25. 1201

    Constantia

    Siege · against Byzantium · Kaloyan

    Today's Simeonovgrad; taken without much effort.

    Angelov & Cholpanov, p. 111 · Bozhilov & Gyuzelev, p. 641 · Bozhilov, p. 45

    Won
  26. 1201

    Varna

    24 March · Siege · against Byzantium · Kaloyan

    Stormed on Good Friday after a three-day siege.

    Angelov & Cholpanov, p. 115 · Bozhilov & Gyuzelev, p. 641 · Jr., p. 49

    Won
  27. 1202

    End of Chrysos' principality

    Campaign · against Byzantium · Dobromir Chrysos

    After his raid to the Peloponnese the Byzantines take back Strumica and his other forts.

    Angelov & Cholpanov, p. 110 · Jr., p. 50

    Lost
  28. 1203

    War with Hungary on the Morava

    Campaign · against Hungary · Kaloyan

    Kaloyan recovers Belgrade and Braničevo.

    Angelov & Cholpanov, p. 115

    Won
  29. 1205

    Adrianople

    14 April · Battle · against Latin Empire · Kaloyan

    Emperor Baldwin is captured and Louis of Blois killed.

    Angelov & Cholpanov, p. 117 · Bozhilov & Gyuzelev, p. 662 · Jr., p. 99 · Nicol, p. 32 · Bozhilov, p. 51

    Won
  30. 1205

    The pursuit through Thrace

    Campaign · against Latin Empire · Kaloyan

    Taken and razed: Karyoupolis, Heraclea, Rhaidestos, Panion, Traianopolis, Mosynopolis, Peritheorion.

    Angelov & Cholpanov, p. 122 · Jr., p. 101

    Won
  31. 1205

    Serres

    June · Siege · against Latin Empire · Kaloyan

    A fight before the town, then the citadel surrenders to Kaloyan's mercy.

    Angelov & Cholpanov, p. 123 · Bozhilov & Gyuzelev, p. 663 · Jr., p. 102

    Won
  32. 1205

    Boniface's detachment at Serres

    Battle · against Latin Empire · Kaloyan

    The force sent toward Serres is routed by the Cumans.

    Angelov & Cholpanov, p. 124

    Won
  33. 1205

    First attempt on Thessaloniki

    Siege · against Latin Empire · Kaloyan

    The lower town is briefly taken, but the attempt fails.

    Angelov & Cholpanov, p. 123 · Jr., p. 102

    Lost
  34. 1205

    Philippopolis

    Siege · against Latin Empire · Kaloyan

    The city, held by Alexios Aspietes, is taken and punished.

    Angelov & Cholpanov, p. 124 · Bozhilov & Gyuzelev, p. 664

    Won
  35. 1206

    Rusion

    31 January · Battle · against Latin Empire · Kaloyan

    The constable Thierry de Termonde's force is destroyed; about ten of 120 knights escape.

    Angelov & Cholpanov, p. 124 · Bozhilov & Gyuzelev, p. 664 · Bozhilov, p. 64

    Won
  36. 1206

    Kaloyan's Thracian campaign

    Campaign · against Latin Empire · Kaloyan

    Apros stormed, Rhaidestos surrenders; Panion, Heraclea, Daonion, Tzurulon and Athyra fall.

    Angelov & Cholpanov, p. 124

    Won
  37. 1206

    First siege of Didymoteicho

    June · Siege · against Latin Empire · Kaloyan

    Kaloyan diverts the Maritsa and breaches the walls, but withdraws as Henry approaches.

    Angelov & Cholpanov, p. 125 · Bozhilov & Gyuzelev, p. 665 · Jr., p. 104 · Bozhilov, p. 64

    Lost
  38. 1206

    Second siege of Didymoteicho

    Siege · against Latin Empire · Kaloyan

    The town is taken and razed.

    Angelov & Cholpanov, p. 127 · Jr., p. 104

    Won
  39. 1206

    Repulsed at Adrianople

    Battle · against Latin Empire · Kaloyan

    The Latins drive the Bulgarians off and pursue them to Beroe.

    Angelov & Cholpanov, p. 127

    Lost
  40. 1206

    Henry's raid

    Campaign · against Latin Empire · Kaloyan

    Henry takes Beroe, Aetos, Thermopolis and Anchialos; one Latin detachment is beaten in the passes.

    Angelov & Cholpanov, p. 127

    Lost
  41. 1207

    Siege of Adrianople

    April · Siege · against Latin Empire · Kaloyan

    For all its 33 trebuchets the siege fails when the Cumans leave.

    Angelov & Cholpanov, p. 128 · Jr., p. 105

    Lost
  42. 1207

    Death of Boniface of Montferrat

    4 September · Battle · against Latin Empire · Kaloyan

    The king of Thessaloniki is ambushed north of Mosynopolis and killed.

    Angelov & Cholpanov, p. 129 · Jr., p. 105 · Nicol, p. 32

    Won
  43. 1207

    Siege of Thessaloniki

    October · Siege · against Latin Empire · Kaloyan

    Kaloyan is killed under the walls and the siege abandoned.

    Angelov & Cholpanov, p. 129 · Bozhilov & Gyuzelev, p. 668 · Jr., p. 105

    Lost
  44. 1208

    Ambush near Rusion

    Battle · against Latin Empire · Boril

    Three hundred Vlachs beat Henry's vanguard.

    Angelov & Cholpanov, p. 130

    Won
  45. 1208

    Beroe

    Battle · against Latin Empire · Boril

    The sources disagree: the military history counts it a Bulgarian success, Fine and Božilov an indecisive fight.

    Angelov & Cholpanov, p. 130 · Bozhilov & Gyuzelev, p. 685 · Jr., p. 111

    Drawn
  46. 1208

    Philippopolis

    31 July · Battle · against Latin Empire · Boril

    Boril is defeated. Božilov gives 31 July, the military history 1 August.

    Angelov & Cholpanov, p. 131 · Bozhilov & Gyuzelev, p. 685 · Jr., p. 111 · Bozhilov, p. 70

    Lost
  47. 1211

    Revolt in Vidin

    Campaign · Boril

    Boril puts the revolt down with Hungarian help.

    Angelov & Cholpanov, p. 132 · Jr., p. 117

    Civil war
  48. 1211

    Pelagonia

    Battle · against Latin Empire · Boril

    Boril and Strez are beaten by the Thessalonian barons and Michael of Epirus on the plain of Bitola.

    Angelov & Cholpanov, p. 132 · Bozhilov & Gyuzelev, p. 692 · Jr., p. 117 · Bozhilov, p. 99

    Lost
  49. 1211

    Melnik

    Siege · against Latin Empire · Boril

    Boril besieges Alexios Slav, and is then beaten by the Latins and Slav.

    Angelov & Cholpanov, p. 132

    Lost
  50. 1214

    Campaign on Niš

    Campaign · against Serbia · Boril

    A night panic in camp breaks up the Bulgarian-Latin army.

    Angelov & Cholpanov, p. 133

    Lost
  51. 1218

    Siege of Tarnovo

    Siege · Ivan Asen II

    Ivan Asen II besieges Boril for seven months and takes the throne.

    Angelov & Cholpanov, p. 134 · Bozhilov & Gyuzelev, p. 697 · Bozhilov, p. 73

    Civil war
  52. 1230

    Klokotnitsa

    9 March · Battle · against Epirus · Ivan Asen II

    Theodore Komnenos is captured; the tsardom reaches from the Black Sea to the Adriatic. Fine places it in April.

    Angelov & Cholpanov, p. 135 · Bozhilov & Gyuzelev, p. 709 · Jr., p. 142 · Nicol, p. 34 · Bozhilov, p. 96

    Won
  53. 1232

    Hungarian siege of Vidin

    Siege · against Hungary · Ivan Asen II

    The Hungarians take Belgrade and Braničevo; Alexander is beaten before the walls, but Vidin holds.

    Jr., p. 147

    Drawn
  54. 1235

    Conquest of Eastern Thrace

    Campaign · against Latin Empire · Ivan Asen II

    Together with Nicaea the Bulgarians take the lands from Gallipoli to Tzurulon.

    Angelov & Cholpanov, p. 138 · Jr., p. 148

    Won
  55. 1235

    Siege of Constantinople

    Siege · against Latin Empire · Ivan Asen II

    Geoffrey of Villehardouin's fleet breaks the blockade.

    Angelov & Cholpanov, p. 139 · Bozhilov & Gyuzelev, p. 728 · Jr., p. 148 · Nicol, p. 34

    Lost
  56. 1237

    Tzurulon

    Siege · against Nicaea · Ivan Asen II

    Now allied with the Latins, Ivan Asen abandons the siege on news of the tsaritsa's death.

    Angelov & Cholpanov, p. 139 · Bozhilov & Gyuzelev, p. 729 · Jr., p. 149 · Bozhilov, p. 104

    Lost
  57. 1241

    Tatar attack repulsed

    Battle · against Tatars · Ivan Asen II

    Only one uncertain source speaks of this victory.

    Angelov & Cholpanov, p. 139 · Bozhilov & Gyuzelev, p. 730

    Won
  58. 1242

    The Tatars returning from Hungary

    Raid · against Tatars · Kaliman Asen I

    The horde crosses Bulgaria, lays it waste and imposes tribute.

    Jr., p. 163 · Nicol, p. 43

    Lost
  59. 1246

    Vatatzes' campaign

    Campaign · against Nicaea · Michael II Asen

    In three months Nicaea takes the lands south of the Balkan range; Serres falls by Dragota's treachery.

    Bozhilov & Gyuzelev, p. 736 · Jr., p. 174 · Nicol, p. 44

    Lost
  60. 1254

    Raid into Serbia

    Raid · against Serbia · Michael II Asen

    Allied with Dubrovnik, the army reaches the Lim and plunders Bijelo Polje; the peace restores the borders.

    Bozhilov & Gyuzelev, p. 739 · Jr., p. 219

    Drawn
  61. 1254

    Michael Asen's Rhodope campaign

    Campaign · against Nicaea · Michael II Asen

    Stenimachos, Perushtitsa, Krichim, Tsepina, Ustra, Perperek and other forts are won back.

    Angelov & Cholpanov, p. 146

    Won
  62. 1254

    Panic on the Maritsa

    Battle · against Nicaea · Michael II Asen

    The Nicaean vanguard scatters the Bulgarian outposts and the army withdraws; Beroe is taken.

    Angelov & Cholpanov, p. 149 · Bozhilov & Gyuzelev, p. 740

    Lost
  63. 1255

    Siege of Tsepina

    Siege · against Nicaea · Michael II Asen

    Theodore II Laskaris fails to take the fortress.

    Angelov & Cholpanov, p. 149

    Won
  64. 1255

    Ambush near Tsepina

    Battle · against Nicaea · Michael II Asen

    Strategopoulos' and Tornikes' column loses its baggage.

    Angelov & Cholpanov, p. 150

    Won
  65. 1255

    Melnik and the Rupel gorge

    Battle · against Nicaea · Dragota

    Dragota's rising ends with his palisade turned and his death.

    Angelov & Cholpanov, p. 150

    Lost
  66. 1255

    Veles

    Siege · against Nicaea · Michael II Asen

    The garrison surrenders.

    Angelov & Cholpanov, p. 151

    Lost
  67. 1255

    Second march on Tsepina

    Campaign · against Nicaea · Michael II Asen

    A snowstorm at Makrolivada turns the emperor back.

    Angelov & Cholpanov, p. 151

    Won
  68. 1256

    Cuman raid near Didymoteicho

    Raid · against Nicaea · Michael II Asen

    Manuel Laskaris flees and Constantine Margarites is captured; the Cumans winter in Thrace.

    Angelov & Cholpanov, p. 151 · Bozhilov & Gyuzelev, p. 741

    Won
  69. 1256

    Skirmishes at Bulgarophygon

    Campaign · against Nicaea · Michael II Asen

    No pitched battle; the peace brokered by Rostislav cedes Tsepina.

    Angelov & Cholpanov, p. 152 · Jr., p. 177

    Drawn
  70. 1257

    Mesembria

    14 June · Siege · against Venice · Constantine Tih Asen

    Latins on Venetian galleys take and plunder the town.

    Angelov & Cholpanov, p. 152 · Jr., p. 189

    Lost
  71. 1257

    The struggle with Mitso

    Campaign · Constantine Tih Asen

    Angelov & Cholpanov, p. 152

    Civil war
  72. 1260

    Vidin taken back from Rostislav

    Campaign · against Hungary · Constantine Tih Asen

    Constantine Tih recovers Vidin and attacks the Banate of Severin.

    Jr., p. 191

    Won
  73. 1260

    Banate of Severin

    Battle · against Hungary · Constantine Tih Asen

    Master Lawrence routs the Bulgarian army.

    Angelov & Cholpanov, p. 152 · Bozhilov & Gyuzelev, p. 753

    Lost
  74. 1261

    Stephen V's campaign

    Campaign · against Hungary · Constantine Tih Asen

    The Hungarians reach the mouth of the Iskar and Tarnovo, and besiege Lom.

    Angelov & Cholpanov, p. 152 · Jr., p. 192

    Lost
  75. 1262

    Campaign in south-east Thrace

    Campaign · against Byzantium · Constantine Tih Asen

    Skopelos, Petra, Skopos and Bryse are taken.

    Angelov & Cholpanov, p. 152

    Won
  76. 1263

    Michael Glabas' campaign

    Campaign · against Byzantium · Constantine Tih Asen

    Byzantium takes Agathopolis, Sozopolis, Anchialos, Philippopolis and the coastal forts.

    Angelov & Cholpanov, p. 153 · Bozhilov & Gyuzelev, p. 753 · Jr., p. 194

    Lost
  77. 1263

    Before Mesembria

    Battle · against Byzantium · Constantine Tih Asen

    Glabas beats the tsar as he besieges Mitso in the town; Manuel Philes adds a second defeat at Agathopolis.

    Angelov & Cholpanov, p. 155 · Bozhilov & Gyuzelev, p. 753

    Lost
  78. 1264

    Ainos

    Siege · against Byzantium · Constantine Tih Asen

    With the Tatars the tsar ravages Thrace; the town hands over Sultan Izz al-Din in return for a withdrawal.

    Angelov & Cholpanov, p. 155 · Bozhilov & Gyuzelev, p. 754 · Jr., p. 195

    Won
  79. 1266

    The Hungarians take Vidin

    Campaign · against Hungary · Constantine Tih Asen

    Stephen V beats the Bulgarian army and takes Vidin, Oryahovo and Pleven.

    Angelov & Cholpanov, p. 156 · Bozhilov & Gyuzelev, p. 755 · Jr., p. 196

    Lost
  80. 1271

    Nogai's raid

    Raid · against Tatars · Constantine Tih Asen

    Nogai's answer to Constantine's raid into Thrace lays the country waste.

    Jr., p. 198 · Angelov & Cholpanov, p. 156

    Lost
  81. 1277

    Ivaylo drives off the Tatars

    Battle · against Tatars · Ivailo

    Ivaylo's band beats Tatar parties and drives them over the Danube.

    Angelov & Cholpanov, p. 158 · Bozhilov & Gyuzelev, p. 761 · Jr., p. 213

    Won
  82. 1277

    Ivaylo kills Constantine Tih

    Battle · Ivailo

    Angelov & Cholpanov, p. 158 · Bozhilov & Gyuzelev, p. 761 · Jr., p. 213

    Civil war
  83. 1278

    Glabas' coastal campaign

    Campaign · against Byzantium · Ivailo

    Emona, Vicha, Kozyak, Galata, Varna, Provadia and Preslav fall.

    Angelov & Cholpanov, p. 161

    Lost
  84. 1278

    Siege of Byalgrad

    Siege · against Byzantium · Ivailo

    Voivode Damyan holds the fortress.

    Angelov & Cholpanov, p. 161

    Won
  85. 1278

    Against Kasim beg's Tatars

    Battle · against Tatars · Ivailo

    Ivaylo beats them, and skirmishing drives Glabas back to Aetos.

    Angelov & Cholpanov, p. 164

    Won
  86. 1278

    Pirgitsa

    Battle · against Byzantium · Ivailo

    Ivaylo is caught between the armies of Glabas and Ivan Asen III.

    Angelov & Cholpanov, p. 165

    Lost
  87. 1279

    Tarnovo opens its gates

    February · Siege · against Byzantium · Ivailo

    Byzantines and Nogai Tatars besiege the city from the autumn; on a rumour of Ivaylo's death it is handed to Ivan Asen III.

    Angelov & Cholpanov, p. 166 · Jr., p. 215

    Lost
  88. 1279

    Siege of Drastar

    Siege · against Byzantium · Ivailo

    For three months the Byzantines fail to take the town where Ivaylo has shut himself in.

    Angelov & Cholpanov, p. 166 · Jr., p. 216

    Won
  89. 1279

    Devina

    17 July · Battle · against Byzantium · Ivailo

    Murin's army of ten thousand is destroyed. Fine gives 17 June.

    Angelov & Cholpanov, p. 167 · Bozhilov & Gyuzelev, p. 764 · Jr., p. 216 · Bozhilov, p. 250

    Won
  90. 1279

    Aprin's defeat

    15 August · Battle · against Byzantium · Ivailo

    Aprin's five thousand are destroyed in Sredna Gora. Fine gives 5 August.

    Angelov & Cholpanov, p. 167 · Bozhilov & Gyuzelev, p. 764 · Jr., p. 216 · Bozhilov, p. 250

    Won
  91. 1280

    The victory of July 1280

    July · Battle · against Byzantium · George Terter I

    The remnants of the beaten Byzantine army reach Athos in the autumn.

    Jr., p. 210

    Won
  92. 1285

    Nogai's devastating raid

    Raid · against Tatars · George Terter I

    Terter accepts Nogai's overlordship and gives his son as hostage.

    Angelov & Cholpanov, p. 170 · Bozhilov & Gyuzelev, p. 789 · Jr., p. 243

    Lost
  93. 1292

    The Tatar raid of 1292

    Raid · against Tatars · George Terter I

    Terter flees to Byzantium and Smilets becomes tsar.

    Angelov & Cholpanov, p. 170 · Jr., p. 244

    Lost
  94. 1292

    Shishman against Milutin

    Campaign · against Serbia · Shishman

    The Vidin despot's raid burns Žiča, but his army is routed and Milutin takes Vidin.

    Bozhilov & Gyuzelev, p. 782 · Jr., p. 239

    Lost
  95. 1301

    Radoslav's defeat

    Battle · against Byzantium · Theodore Svetoslav

    Eltimir beats the Byzantine candidate for the throne, captures him and has him blinded.

    Bozhilov & Gyuzelev, p. 801 · Jr., p. 247

    Won
  96. 1304

    The forts below the Haemus

    Campaign · against Byzantium · Theodore Svetoslav

    Yambol, Lardea, Ktenia, Rusokastro, Mesembria and Sozopolis are taken.

    Angelov & Cholpanov, p. 170 · Bozhilov & Gyuzelev, p. 803 · Jr., p. 247

    Won
  97. 1304

    Skafida

    Battle · against Byzantium · Theodore Svetoslav

    The bridge collapses under the retreating Byzantines; Anchialos and Agathopolis open their gates.

    Angelov & Cholpanov, p. 170 · Bozhilov & Gyuzelev, p. 803 · Jr., p. 247

    Won
  98. 1305

    Fight near Sozopolis

    Battle · against Byzantium · Theodore Svetoslav

    One of the smaller engagements in Michael IX's campaign.

    Jr., p. 247

    Lost
  99. 1305

    Michael IX's campaign

    Campaign · against Byzantium · Theodore Svetoslav

    Michael IX ravages the land to Ryahovo, but a Bulgarian victory breaks his lines and the army plunders toward Adrianople.

    Angelov & Cholpanov, p. 172 · Bozhilov & Gyuzelev, p. 804 · Jr., p. 247

    Won
  100. 1319

    The Tatar raid of 1319

    Raid · against Tatars · Theodore Svetoslav

    Jr., p. 247

    Lost
  101. 1322

    Philippopolis taken by surprise

    Siege · against Byzantium · George Terter II

    George II Terter takes the city and much of northern Thrace.

    Angelov & Cholpanov, p. 173 · Bozhilov & Gyuzelev, p. 814 · Jr., p. 269

    Won
  102. 1322

    The night attack

    Battle · against Byzantium · George Terter II

    The army that had plundered round Adrianople is surprised and beaten on its way back.

    Bozhilov & Gyuzelev, p. 814

    Lost
  103. 1322

    Siege of Philippopolis

    Siege · against Byzantium · George Terter II

    Ivan Rusina's garrison holds out for nearly four months; the German siege tower sinks into the ditch.

    Angelov & Cholpanov, p. 173 · Bozhilov & Gyuzelev, p. 817 · Jr., p. 287

    Won
  104. 1323

    Michael Shishman recovers the south

    Campaign · against Byzantium · Michael III Shishman Asen

    With the Tatars the tsar breaks the siege, and the towns between Sliven and Mesembria surrender.

    Angelov & Cholpanov, p. 177 · Jr., p. 287

    Won
  105. 1323

    Philippopolis lost

    Siege · against Byzantium · Michael III Shishman Asen

    George Bryennios takes the city in the summer.

    Angelov & Cholpanov, p. 178 · Jr., p. 287

    Lost
  106. 1323

    Against Voisil

    Battle · against Byzantium · Michael III Shishman Asen

    The tsar beats the Byzantine vassal at Kopsis and plunders Thrace for twelve days.

    Angelov & Cholpanov, p. 178 · Bozhilov & Gyuzelev, p. 816 · Jr., p. 287

    Won
  107. 1324

    Raid on Berrhoia

    Raid · against Byzantium · Michael III Shishman Asen

    Followed by a Byzantine counter-raid.

    Jr., p. 287

    Outcome unknown
  108. 1328

    Diampolis

    June · Siege · against Byzantium · Michael III Shishman Asen

    The tsar withdraws before Andronikos III, who storms and razes Yambol.

    Angelov & Cholpanov, p. 179 · Nicol, p. 201

    Lost
  109. 1328

    Boukelon and Provaton

    September · Campaign · against Byzantium · Michael III Shishman Asen

    Boukelon is taken; for a month the two armies face each other, then make peace.

    Angelov & Cholpanov, p. 179 · Bozhilov & Gyuzelev, p. 830 · Nicol, p. 201

    Drawn
  110. 1330

    Zemen

    Siege · against Serbia · Michael III Shishman Asen

    Angelov & Cholpanov, p. 180

    Won
  111. 1330

    Velbazhd

    28 July · Battle · against Serbia · Michael III Shishman Asen

    Caught foraging, the army is routed and Michael Shishman killed.

    Angelov & Cholpanov, p. 181 · Bozhilov & Gyuzelev, p. 843 · Jr., p. 289 · Nicol, p. 209 · Bozhilov, p. 139

    Lost
  112. 1330

    Mraka and IzvorTradition

    Battle · against Serbia · Michael III Shishman Asen

    By tradition Belaur's Vidin army halts the Serbian advance.

    Angelov & Cholpanov, p. 183

    Won
  113. 1330

    Andronikos III takes the coast

    Campaign · against Byzantium · Ivan Stefan

    Anchialos, Mesembria, Aetos, Ktenia, Rusokastro and Yambol fall.

    Bozhilov & Gyuzelev, p. 846 · Jr., p. 290 · Nicol, p. 209

    Lost
  114. 1331

    Belaur's revolt

    Campaign · Ivan Alexander

    Ivan Alexander crushes it with Tatar mercenaries.

    Angelov & Cholpanov, p. 186 · Bozhilov & Gyuzelev, p. 860 · Jr., p. 291

    Civil war
  115. 1331

    Tatar raid on Vidin

    Raid · against Tatars · Ivan Alexander

    Jr., p. 247

    Lost
  116. 1331

    The Thracian towns recovered

    Campaign · against Byzantium · Ivan Alexander

    With Tatar help Ivan Alexander takes everything back but Mesembria.

    Angelov & Cholpanov, p. 186 · Jr., p. 292

    Won
  117. 1332

    The fight in the defile

    Battle · against Byzantium · Ivan Alexander

    Andronikos III is twice thrown back before Rusokastro.

    Angelov & Cholpanov, p. 186

    Won
  118. 1332

    Rusokastro

    18 July · Battle · against Byzantium · Ivan Alexander

    The tsardom's last great victory over Byzantium. The Asen genealogy dates it 1331.

    Angelov & Cholpanov, p. 187 · Bozhilov & Gyuzelev, p. 857 · Bozhilov, p. 135

    Won
  119. 1341

    The detachments near Didymoteicho

    Raid · against Byzantium · Ivan Alexander

    The scattered parties are beaten by the pinkernes Angelos and by a Turkish band on the coast.

    Angelov & Cholpanov, p. 198 · Bozhilov & Gyuzelev, p. 875 · Jr., p. 314

    Lost
  120. 1341

    Umur's fleet at the Danube

    Campaign · against Byzantium · Ivan Alexander

    Under the threat Ivan Alexander withdraws his troops and renews the treaty.

    Jr., p. 311 · Nicol, p. 221

    Lost
  121. 1342

    Blockade of Didymoteicho

    Siege · against Byzantium · Ivan Alexander

    The siege is lifted when Umur's ships sail up the Maritsa.

    Angelov & Cholpanov, p. 200 · Bozhilov & Gyuzelev, p. 878 · Jr., p. 313

    Lost
  122. 1344

    Crossing the Maritsa

    June · Battle · against Byzantium · Ivan Alexander

    Kantakouzenos catches the tsar crossing the river and inflicts losses.

    Angelov & Cholpanov, p. 202

    Lost
  123. 1344

    Abdera

    Battle · against Turks of Aydin · Momchil

    Momchil beats Umur's Turks and burns their ships.

    Angelov & Cholpanov, p. 193 · Bozhilov & Gyuzelev, p. 882

    Won
  124. 1344

    Mosynopolis

    Battle · against Byzantium · Momchil

    Momchil storms the camp and Kantakouzenos barely escapes.

    Angelov & Cholpanov, p. 194 · Bozhilov & Gyuzelev, p. 882

    Won
  125. 1345

    Umur plunders Bulgaria

    Raid · against Turks of Aydin · Ivan Alexander

    Jr., p. 322

    Lost
  126. 1345

    Peritheorion

    7 July · Battle · against Byzantium · Momchil

    Kantakouzenos and Umur destroy Momchil's army; he is killed under the walls.

    Angelov & Cholpanov, p. 195 · Bozhilov & Gyuzelev, p. 882 · Jr., p. 322 · Bozhilov, p. 155

    Lost
  127. 1346

    Selymbria

    Battle · against Byzantium · Dobrotitsa

    Sent to help the regency, Dobrotitsa and his brother Theodore are routed.

    Angelov & Cholpanov, p. 205 · Bozhilov & Gyuzelev, p. 885 · Bozhilov, p. 155

    Lost
  128. 1347

    Midia

    Siege · against Byzantium · Dobrotitsa

    Dobrotitsa surrenders the town to Kantakouzenos and John V.

    Angelov & Cholpanov, p. 205 · Bozhilov & Gyuzelev, p. 885

    Lost
  129. 1350

    Suleiman across the Maritsa

    Raid · against Ottomans · Ivan Alexander

    One of a run of Turkish raids from 1344 to 1352, with much booty and many captives.

    Angelov & Cholpanov, p. 218 · Jr., p. 340

    Lost
  130. 1352

    Battle near Didymoteicho

    October · Battle · against Ottomans · Ivan Alexander

    Suleiman's Ottomans crush John V's allies. Nicol names a Serbian and a Bulgarian army; Fine doubts the Bulgarian part, and the military history has the Bulgarians withdraw without fighting.

    Nicol, p. 271 · Jr., p. 343 · Angelov & Cholpanov, p. 206

    Lost
  131. ~1355

    Death of Michael Asen

    Battle · against Ottomans · Ivan Alexander

    The tsar's son is killed fighting Suleiman's raiders; many captives are carried off to Gallipoli.

    Angelov & Cholpanov, p. 219 · Bozhilov & Gyuzelev, p. 905

    Lost
  132. 1363

    Philippopolis and Beroe

    Siege · against Ottomans · Ivan Alexander

    The Turks take Stara Zagora and Plovdiv.

    Angelov & Cholpanov, p. 219 · Jr., p. 396

    Lost
  133. 1364

    Anchialos and Mesembria

    Siege · against Byzantium · Ivan Alexander

    John V takes Anchialos and besieges Mesembria by land and sea; under the peace both towns stay Bulgarian.

    Angelov & Cholpanov, p. 206 · Bozhilov & Gyuzelev, p. 891

    Drawn
  134. 1365

    Vidin

    2 June · Siege · against Hungary · Ivan Sratsimir

    Louis I takes the city in four days, and Ivan Sratsimir is led off captive.

    Angelov & Cholpanov, p. 206 · Bozhilov & Gyuzelev, p. 892 · Jr., p. 384 · Nicol, p. 296

    Lost
  135. 1366

    Amadeus of Savoy's campaign

    October · Campaign · against Amadeus of Savoy · Ivan Alexander

    Ahtopol, Sozopolis, Skafida, Rusokastro, Anchialos, Mesembria and Emona fall.

    Angelov & Cholpanov, p. 207 · Bozhilov & Gyuzelev, p. 894 · Nicol, p. 299

    Lost
  136. 1366

    Aetos

    Siege · against Amadeus of Savoy · Ivan Alexander

    The assault fails and Antonio Visconti is taken prisoner.

    Angelov & Cholpanov, p. 209

    Won
  137. 1366

    Varna

    25 October · Siege · against Amadeus of Savoy · Ivan Alexander

    The assaults fail and the siege is lifted after talks.

    Angelov & Cholpanov, p. 209 · Bozhilov & Gyuzelev, p. 894 · Nicol, p. 299

    Won
  138. 1371

    Chernomen

    26 September · Battle · against Ottomans

    The Ottomans destroy the army of Vukašin and Uglješa. There is no sure evidence of Bulgarian participation.

    Angelov & Cholpanov, p. 219 · Bozhilov & Gyuzelev, p. 969 · Jr., p. 397 · Bozhilov, p. 216

    No Bulgarian army
  139. 1371

    Murad presses Ivan Shishman

    Campaign · against Ottomans · Ivan Shishman

    The tsar is pushed north of the Balkan range, becomes a vassal and gives his sister Tamar to the sultan.

    Angelov & Cholpanov, p. 220 · Bozhilov & Gyuzelev, p. 972 · Bozhilov, p. 216

    Lost
  140. 1373

    The Tundzha forts

    Campaign · against Ottomans · Ivan Shishman

    Timurtash takes Elhovo, Boyadzhik and Voynika.

    Angelov & Cholpanov, p. 220

    Lost
  141. 1373

    Yambol

    Siege · against Ottomans · Ivan Shishman

    The town capitulates after an epidemic.

    Angelov & Cholpanov, p. 220

    Lost
  142. 1373

    Lala Shahin's campaign

    Campaign · against Ottomans · Ivan Shishman

    Kostenets, Urvich, Ihtiman and Samokov fall.

    Angelov & Cholpanov, p. 221

    Lost
  143. 1375

    Conquest of the RhodopesTradition

    Campaign · against Ottomans · Ivan Shishman

    Rakovitsa, Tsepina, Batkun, Perushtitsa and more forts; the account rests mostly on local tradition.

    Angelov & Cholpanov, p. 224

    Lost
  144. ~1375

    The Struma and Mesta fortsTradition

    Campaign · against Ottomans · Ivan Shishman

    Petrich, Gradevo, Krupnik, Momina Kula and Razlog.

    Angelov & Cholpanov, p. 227

    Lost
  145. ~1375

    TopkoriaTradition

    Battle · against Ottomans · Voivode Momchil

    By tradition the voivode routs a Turkish band and kills its leader Orhan.

    Angelov & Cholpanov, p. 228

    Won
  146. ~1375

    KasapkaTradition

    Battle · against Ottomans · Voivodes Blagoy and Radoy

    By tradition the voivodes are beaten by Sinan Pasha.

    Angelov & Cholpanov, p. 228

    Lost
  147. 1380

    First siege of Sofia

    Siege · against Ottomans · Ivan Shishman

    Lala Shahin fails to take ban Yanuka's city.

    Angelov & Cholpanov, p. 228

    Won
  148. 1382

    Fall of Sofia

    Siege · against Ottomans · Ivan Shishman

    Fine dates the capture 1385.

    Angelov & Cholpanov, p. 229 · Jr., p. 425

    Lost
  149. 1387

    Velbazhd and Melnik

    Campaign · against Ottomans · Ivan Shishman

    Angelov & Cholpanov, p. 227

    Lost
  150. 1388

    Ali Pasha's campaign

    Campaign · against Ottomans · Ivan Shishman

    Shumen, Madara, Venchan, Provadia, Silistra and Svishtov fall; the tsar, besieged in Nikopol, accepts a harsh peace. Nicol puts the campaign in early 1389.

    Angelov & Cholpanov, p. 230 · Bozhilov & Gyuzelev, p. 989 · Jr., p. 425 · Nicol, p. 322

    Lost
  151. 1388

    Varna holds

    Siege · against Ottomans · Ivanko son of Dobrotitsa

    Ali Pasha's attempt on Varna fails.

    Angelov & Cholpanov, p. 230 · Bozhilov & Gyuzelev, p. 989

    Won
  152. 1389

    Kosovo

    15 June · Battle · against Ottomans

    A battle between Serbs and Ottomans. The military history mentions Bulgarian contingents on the allied left.

    Angelov & Cholpanov, p. 235 · Jr., p. 428 · Nicol, p. 322 · Bozhilov, p. 227

    No Bulgarian army
  153. 1393

    Fall of Tarnovo

    17 July · Siege · against Ottomans · Ivan Shishman

    The capital falls after a three-month siege and the tsardom is annexed.

    Angelov & Cholpanov, p. 238 · Jr., p. 440 · Nicol, p. 333 · Bozhilov, p. 227

    Lost
  154. 1393

    The last strongholds

    Campaign · against Ottomans · Ivan Shishman

    Pleven, Vratsa, Bozhenishki Urvich, Lovech, Shipka, Krn and Maglizh.

    Angelov & Cholpanov, p. 239

    Lost
  155. 1395

    Nikopol and the death of Ivan Shishman

    Siege · against Ottomans · Ivan Shishman

    Most sources place the tsar's death after the battle of Rovine (1395); Nicol two years after his capture at Nikopol.

    Angelov & Cholpanov, p. 239 · Nicol, p. 333 · Bozhilov, p. 228

    Lost
  156. 1395

    Little Nikopol

    Siege · against Ottomans

    Sigismund takes the fortress from the Ottomans.

    Angelov & Cholpanov, p. 247

    No Bulgarian army
  157. 1396

    Vidin opens to the crusade

    Siege · against Ottomans · Ivan Sratsimir

    Ivan Sratsimir lets the crusaders in and the Ottoman garrison is killed.

    Angelov & Cholpanov, p. 242 · Nicol, p. 337

    Won
  158. 1396

    Oryahovo

    Siege · against Ottomans · The townspeople of Oryahovo

    As the crusaders attack, the local Bulgarians drive out the Ottoman garrison.

    Angelov & Cholpanov, p. 244 · Nicol, p. 337

    Won
  159. 1396

    Nicopolis

    25 September · Battle · against Ottomans · Ivan Sratsimir

    Sigismund's crusading army is destroyed; Sratsimir had fought on its side.

    Angelov & Cholpanov, p. 245 · Jr., p. 442 · Nicol, p. 337 · Bozhilov, p. 205

    Lost
  160. 1396

    End of the Vidin tsardom

    Siege · against Ottomans · Ivan Sratsimir

    Bayezid takes Vidin and leads Sratsimir away captive.

    Angelov & Cholpanov, p. 249 · Jr., p. 442 · Nicol, p. 337

    Lost
  161. ~1396

    Kaliakra and Urdoviza

    Siege · against Ottomans

    Kaliakra is taken and Urdoviza surrenders on terms, in 1396 or 1397.

    Angelov & Cholpanov, p. 240

    Lost