Ivan III of Russia
The Muscovite–Lithuanian Wars renewed in 1500. In 1501, Ivan III of Russia sent a new force under the command of 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.