The Battle of Mstislavl took place on 4 November 1501 between the forces of the Grand Duchy of Lithuania and the forces of the Grand Duchy of Moscow and Principality of Novgorod-Seversk. The Lithuanian forces were defeated.
The Muscovite–Lithuanian Wars renewed in 1500. In 1501, Ivan III of Russia sent a new force under the command of Semyon Mozhayskiy towards Mstislavl. Local princes Mstislavsky together with Ostap Dashkevych organized the defense and were badly beaten on 4 November. They retreated to Mstislavl and Mozhayskiy decided not to attack the castle. Instead, Russian forces besieged the city and pillaged surrounding areas.
Lithuanians organized a relief force, brought by Great Hetman Stanislovas Kęsgaila. Neither Mozhayskiy nor Kęsgaila dared to attack and the Russian forces retreated without a battle.
The main task of the Russians was to prevent the joint military actions of the entire coalition (Lithuania, Livonia and the Great Horde) against Muscovy, as a result of defeating a large group near Mstislavl this task was successfully completed.
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