End of the Second Bulgarian Empire

Ivan Shishman died in 1395 when the Ottomans, led by Bayezid I, took his last fortress Nikopol. In 1396, Ivan Sratsimir joined the Crusade of the Hungarian king Sigismund, but after the Christian army was defeated in the battle of Nicopolis the Ottomans immediately marched on Vidin and seized it, bringing an end to the medieval Bulgarian state.

The Battle of Nicopolis took place on 25 September 1396 and resulted in the rout of an allied crusader army of Hungarian, Croatian, Bulgarian, Wallachian, French, Burgundian, German, and assorted troops (assisted by the Venetian navy) at the hands of an Ottoman force, raising the siege of the Danubian fortress of Nicopolis and leading to the end of the Second Bulgarian Empire. It is often referred to as the Crusade of Nicopolis as it was one of the last large-scale Crusades of the Middle Ages, together with the Crusade of Varna in 1443–1444.