Muscovite–Lithuanian Wars
14th century: Lithuanian expansion

The Grand Duchy of Moscow and Lithuania had fought each other since the reign of Gediminas, who defeated a coalition of Ruthenian princes in the Battle on the Irpin River and seized Kiev, the former capital of Kievan Rus'. By the mid-14th century, an expanding Lithuania had absorbed Chernigov and Severia. Algirdas, the successor of Gediminas, allied with the Principality of Tver and undertook three expeditions against Moscow, attempting to take advantage of the youth of the Grand Prince of Moscow, Dmitry Ivanovich, who nevertheless succeeded in fending off these encroachments.

The first intrusions of Lithuanian troops into the Moscow principality occurred in 1363. In 1368, Algirdas carried out the first major expedition against Moscow. Having devastated the Muscovite borderland, the Lithuanian prince routed the troops of the Prince of Starodub Simeon Dmitrievich Krapiva and Prince of Obolensk Konstantin Yurievich. On November 21, Algirdas routed the Moscow sentry troops on the river Trosna. However, he could not seize the Moscow Kremlin. The troops of Algirdas ruined the area around the city and captured a significant portion of the Muscovite population. In 1370, Algirdas made another expedition against Moscow. He ruined the area around Volok Lamskiy. On December 6, he besieged Moscow and started to devastate the surrounding area. Having received the message that Prince Vladimir Andreevich was coming to help Moscow, Algirdas returned to Lithuania. In 1372 Algirdas attacked the Moscow principality again and reached Lyubutsk. However, the Grand Prince of Moscow Dmitry Ivanovich routed the sentry troops of Algirdas, and the Lithuanians concluded an armistice with Moscow. In 1375, Algirdas devastated the Smolensk principality.

Some Muscovite elements wished to take over all of the land that was formerly of the Kievan Rus', most of which was now in the Lithuanian state. Furthermore, Moscow sought to expand its access to the Baltic Sea, an increasingly important trade route. Thus, the conflict between Lithuania and Moscow was only just beginning.
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