Lithuanian Civil War (1389–92): The Teutonic Knights begin a five-week siege of Vilnius.

The Lithuanian Civil War of 1389–1392 was the second civil conflict between Jogaila, King of Poland and Grand Duke of Lithuania, and his cousin Vytautas. At issue was control of the Grand Duchy of Lithuania, then the largest state in Europe. Jogaila had been crowned King of Poland in 1386; he installed his brother Skirgaila as ruler of Lithuania. Skirgaila proved unpopular and Vytautas attempted to depose him. When his first attempt to take the capital city of Vilnius failed, Vytautas forged an alliance with the Teutonic Knights, their common enemy – just as both cousins had done during the Lithuanian Civil War between 1381 and 1384. Vytautas and the Knights unsuccessfully besieged Vilnius in 1390. Over the next two years it became clear that neither side could achieve a quick victory, and Jogaila proposed a compromise: Vytautas would become Grand Duke and Jogaila would remain Superior Duke. This proposal was formalized in the Ostrów Agreement of 1392, and Vytautas turned against the Knights. He went on to reign as Grand Duke of Lithuania for 38 years, and the cousins remained at peace.

The Teutonic Order is a Catholic religious institution founded as a military society c. 1190 in Acre, Kingdom of Jerusalem. The Order of Brothers of the German House of Saint Mary in Jerusalem was formed to aid Christians on their pilgrimages to the Holy Land and to establish hospitals. Its members have commonly been known as the Teutonic Knights, having historically served as a crusading military order for supporting Catholic rule in the Holy Land and the Northern Crusades during the Middle Ages, as well as supplying military protection for Catholics in Eastern Europe.

Vilnius is the capital of and largest city in Lithuania and the most-populous city in the Baltic states. The city's estimated January 2025 population was 607,667, and the Vilnius urban area has an estimated population of 747,864.