Battles of Medieval Bulgaria

In 1190 Tsar Asen I lured the Byzantine army of Isaac II Angelos into an ambush in the Tryavna pass and destroyed it.

On 14 April 1205 Tsar Kaloyan crushed the Latin Empire's knightly army at Adrianople and captured Emperor Baldwin I.

In 1208 Tsar Boril was defeated by the Latin emperor Henry at Beroe (Stara Zagora).

On 9 March 1230 Tsar Ivan Asen II routed the Epirote ruler Theodore Komnenos at Klokotnitsa and captured him and his court.

In 1235–1236 Tsar Ivan Asen II and the Nicaean emperor John III Vatatzes jointly besieged Latin Constantinople but failed to take it.

Ivaylo's peasant uprising (1277–1280) defeated Tatars, the Tarnovo army and two Byzantine armies before ending with his death.

In 1304 Tsar Theodore Svetoslav routed the Byzantine army at the Skafida river when the bridge collapsed beneath it.

On 28 July 1330 the Serbian army defeated the Bulgarians at Velbazhd; Tsar Michael III Shishman fell in the battle.

On 18 July 1332 Tsar Ivan Alexander defeated the army of Byzantine emperor Andronikos III at Rusokastro.

In 1345 the semi-independent lord Momchil was surrounded and killed at Peritheorion by the forces of Kantakouzenos and the emir Umur.

In 1366 a crusade led by Count Amadeus VI of Savoy seized the Black Sea fortresses of Anchialos and Mesembria from Tsar Ivan Alexander.

On 26 September 1371 the Ottomans crushed the armies of the Serbian rulers Vukašin and Uglješa at Chernomen on the Maritsa.

After a long siege around 1382 the Ottomans captured the strong fortress of Sredets (Sofia).

On 17 July 1393, after a three-month siege, the Ottomans of Sultan Bayezid I took Tarnovo, the capital of the Second Bulgarian Empire.

On 25 September 1396 Sultan Bayezid I crushed the crusader army at Nicopolis — the last great attempt to halt the Ottoman advance.