The Muscovite-Lithuanian Wars was a series of wars fought between the Grand Duchy of Lithuania, allied with the Kingdom of Poland, and the Grand Duchy of Moscow from the 14th to 16th centuries.
In response to Lithuanian attacks on the Russian border in the 13th century, Prince Alexander Nevsky of Novgorod and allied Russian princes invaded Lithuania in 1245, freed all the prisoners, and defeated the Lithuanians at Lake Zizicekoe. The Grand Duchy of Moscow waged its first war against the Lithuanians during the reign of Grand Duke Gediminas, who defeated a coalition of Ruthenian princes at the Battle on the Irpin River in the 1320s and seized Kyiv, the former capital of the Kievan Rus. By the mid-14th century, Lithuania had taken advantage of the Mongols' destruction of the Kievan Rus to absorb Chernigov and Severia, and Duke Algirdas allied with the Principality of Tver and undertook three expeditions against the young Grand Prince Dmitry of Moscow. The Muscovites fought off the Lithuanian encroachments of 1363, 1368, and 1372, although Algirdas sacked Moscow's outskirts in 1370 and devastated the Principality of Smolensk in 1375.
Muscovy's desire to reconquer the lands of the former Kievan Rus and its planned expansion towards the trade routes of the Baltic Sea brought it into conflict with the Muscovites. Although Duke Vasily I of Russia married Grand Duke Vytautas the Great's daughter Sophia of Lithuania, conflict resumed during the 1390s. Vytautas devastated the Principality of Ryazan in 1394, and, in 1402, he quarreled with his son-in-law over control of Smolensk. Vytautas took the city from Prince Yury of Smolensk, forcing the latter to flee to Vasily's court and enlist his assistance against the Lithuanians. Vasily hesitated until Vytautas advanced on Pskov, after which Vasily sent an army to aid the Pskovians. The Russian and Lithuanian armies met near the Ugra River, but neither ruler committed to battle, and a peace ensued, leaving Vytautas in control of Smolensk.
Grand Duke Ivan III of Russia (r. 1462-1505) considered himself an heir to the Byzantine Empire and proclaimed himself sovereign of all Russia, claiming patrimonial rights to the former lands of the Kievan Rus and overthrowing the Golden Horde's "Mongol Yoke" at the Great Stand on the Ugra River in 1480. Moscow annexed Ryazan in 1456, the Novgorod Republic in 1477, and the Principality of Tver in 1483. In 1492, Ivan captured and burned Mtsensk, Lyubutsk, Serpeysk, and Meshchovsk, raided Mosalsk, and attacked Vyazma. Orthodox nobles switched their allegiance to Moscow in exchange for protection from military raids and an end to religious discrimination by the Catholic Lithuanians. Ivan officially declared war in 1493, but an "eternal" peace treaty was concluded with Grand Duke Alexander Jagiellon on 5 February 1494. Lithuania ceded the Principality of Vyazma to the Muscovites, and Alexander married Ivan's daughter Helena of Moscow.
In 1500, Ivan took advantage of a planned Polish-Hungarian campaign against the Ottoman Turks by invading Lithuania. The Muscovites overran Lithuanian fortresses in Bryansk, Vyazma, Dorogobuzh, Toropets, and Putivl, and local nobles joined the Muscovite cause. In 1500, the Lithuanians were heavily defeated at the Battle of Vedrosha, resulting in Poland proposing a union with Lithuania. In 1501, the Lithuanians were again defeated at the Battle of Mstislavl, and the Crimean Tatars destroyed Lithuania's Golden Horde ally by capturing New Sarai in 1502. In 1501, Alex was elected King of Poland. The Livonian Order joined the Lithuanian side shortly after, defeating the Russians at the Battle of the Siritsa River in 1501 and besieging Pskov. In 1502, the Muscovites failed to capture Smolensk, and a six-year truce was concluded in 1503; Lithuania lost a third of its territory, including Chernigov, Novgorod-Seversk, and Starodub, to Moscow. At the same time, the Tatars raided Slutsk, Kletsk, and Nyasvizh, forcing Alexander to fortify Vilnius with a defensive wall in 1522.
In 1506, Vasili III of Russia attempted to claim the Polish throne on Alexander's death, but the Poles and Lithuanians chose Sigismund I the Old as their ruler. In 1507, Sigismund demanded that Moscow return its lost territories, and the Crimean Khanate broke off its alliance with Moscow due to its campaign against Kazan. Khan Menli I Giray authorized the Lithuanians to conquer Novgorod, Peskov, and Ryazan, but Court Marshal Michael Glinski led a rebellion against Sigismund. Glinski allied himself with Vasili, and he captured Mazyr before being defeated near Orsha. In 1508, the Lithuanians and Russians agreed to a new peace with no territorial changes. In 1512, however, Sigismund's demand for Michael Glinski's extradition resulted in a new war, and the Teutonic Order and the Holy Roman Empire allied with Moscow. The Lithuanians took Smolensk in 1514, and Russia experienced several defeats, including the Battle of Orsha and the 1518 siege of Polotsk. In 1522, a new peace treaty was signed.
In 1533, the Polish king took advantage of the accession of the three-year-old Ivan IV to demand that Moscow return the territories conquered by Vasily III. The Poles and Tatars devastated western Russia in 1534, but the Russians invaded Lithuania before being stopped at Lake Sebezh. The Lithuanians and Poles launched a counterattack that took Gomel and Starodub, but they failed to take Sebezh, and the Mucsovites razed Vitebsk. A peace treaty left Sebezh and Zavoloche under Muscovite control.
In 1547, Ivan proclaimed the Tsardom of Russia and resolved to reconquer the ethnically Ruthenian lands of the former Kievan Rus. He engaged with the other Baltic powers in the Livonian War, and the Poles and Lithuanians allied with Denmark against Russia and Sweden before Sweden allied with the Poles and Lithuanians against Russia and Denmark later in the war. In 1570, a ceasefire divided Livonia within the participants, giving Riga to Lithuania. In 1569, Lithuanian pressure to elevate their nobility to have the same rights as the Poles resulted in the formation of a Commonwealth of Poland-Lithuania. Poland-Lithuania reconquered Polotsk in 1579 and Velikiye Luki in 1580 and burned Staraya Russa in 1581, and a 1582 peace forced the Tsar to renounce his claims to Livonia and Polotsk. Peace would hold until the Polish-Russian War of 1609-1618 broke out.