Battle of Vedrosha

The Battle of [the] Vedrosha (Lithuanian: Vedrošos mūšis; Russian: Ведрошская битва) was fought near the Vedrosha river, close to Dorogobuzh (then in the Grand Duchy of Lithuania, now in Russia) on 14 July 1500, during the Second Muscovite–Lithuanian War (1500–1503).

In the battle of Vedrosha, Muscovite forces defeated outnumbered Lithuanian troops attacking them. The Battle of Vedrosha was the first major Muscovite victory over Lithuania in the war of 1500–1503.

The Lithuanian geopolitical situation after the battle was desperate. Alexander of Lithuania unsuccessfully tried to even make the Crimean Khanate under Meñli I Giray and Moldavia under Stephen III begin hostilities against Muscovy, with which they were allied. The only help the Lithuanians received was the Livonian Order's attack on Pskov, which failed due to dysentery.

The battle is mentioned in several Muscovite Chronicles, but these generally confuse details, for example, place names (e.g. Vyazma instead of Vedrosha) and the names of the military leaders.

At the turn of the 15th–16th centuries, the Prince of Moscow, openly interfered in the internal affairs of the Grand Duchy of Lithuania. The Muscovites agitated the Grand Duchy's Eastern Orthodox inhabitants against their Catholic rulers and tried to enflame to renounce Lithuania and join Muscovy. The First Lithuanian–Muscovite War (1487–1494) concluded with a perpetual peace treaty in 1494 between Grand Duke Alexander of Lithuania and Grand Duke Ivan III of Moscow (both descended from the Lithuanian dynasty of the Gediminids).

The "Perpetual Peace" treaty with Moscow meant only a short respite for Lithuania, because Ivan III declared war to Lithuania once more on 3 May 1500 to join its eastern lands to Muscovy. The marriage of Alexander and Elena, daughter of Ivan III, in 1495 did not lead to peaceful Lithuanian-Muscovite relations or a common policy against the Tatars, as was hoped for by some. Alexander's brothers John I Albert and Vladislaus II of Hungary could not help because they were at war with the Ottoman Empire.

The official pretext for the Muscovite declaration of war was the escape of Duke Simeon Ivanovich Belsky to Moscow in 1499. Muscovites declared themselves defenders of the rights of the Eastern Orthodox in Lithuania, and, along with Bielski's escape, provided alleged evidence about attempts of forcefully converting Elena, now Grand Duchess of Lithuania, to Catholicism. They also referred to the activities of Catholic missionaries in the eastern lands of Lithuania where many Orthodox lived.

After the declaration of war, the princes of Chernigov and Novgorod-Seversk defected to Muscovy. The main object contested between Muscovy and Lithuania were the vast territories close to the Dnieper, which was strategically important for communication and trade.