Battle of the Vorskla River The Battle of the Vorskla River was a great battle in the medieval history of Eastern Europe . It was fought on August 12 , 1399 , between the Tatars , under Edigu and Temur Qutlugh , and the armies of Tokhtamysh and Grand Duke Vytautas of Lithuania . The battle ended in a decisive Tatar victory . Background . In late 1380s the relationship between Tokhtamysh , Khan of the Golden Horde , and his former master , Timur , was growing tense . In 1395 , after losing the Tokhtamysh – Timur war , Tokhtamysh was dethroned by the party of Khan Temur Qutlugh and Emir Edigu , supported by Timur . Tokhtamysh escaped to the Grand Duchy of Lithuania and asked Vytautas for assistance in retaking the Horde in exchange for surrendering his suzerainity over Ruthenian lands . This development was in harmony with Vytautas ' ambitions to become ruler of all Rutherian lands . A surviving iarlyk shows that Tokhtamysh had asked for Polish – Lithuanian assistance previously in 1393 . Vytautas ' expeditions . Vytautas gathered a large army which included Lithuanians , Ruthenians , Poles , Moldavians , and Wallachians . To enlist support from the Teutonic Knights , Vytautas signed the Treaty of Salynas , surrendering Samogitia to the Knights . Vytautas ' s son - in - law , Vasily I of Moscow , formally a Tatar vassal , did not join the coalition . The joint forces organized three expeditions into Tatar territories , in 1397 , 1398 , and 1399 . The first expedition reached the Black Sea and Crimea . Vytautas took several thousand captives without much opposition . Half of these captives were settled near Trakai and awarded privileges to practice their faith . Communities of their descendants , Lipka Tatars and Crimean Karaites ( Karaims ) , survive to this day . In 1398 , the army of Vytautas moved from the Dnieper River and attacked northern Crimea , reaching as far east as the River Don . In order to strengthen his position , Vytautas built a castle at the mouth of Dnieper . Inspired by their successes , Vytautas declared a " Crusade against the Tatars " and in May 1399 received blessing from Pope Boniface IX . The papal blessing for the crusade was an important political achievement for Lithuania , a country converted to Christianity only in 1387 and the subject of a hundred - year crusade . The campaign was organized from Kiev . In 1399 , the army of Vytautas once again moved against the Horde along the Dnieper River . On August 5 , his army met the Tatars at the Vorskla River just north of Poltava ( almost same location as the Battle of Poltava of 1709 ) . Battle . Once the two armies met , Temur Qutlugh proposed a three - day ceasefire to allow both sides to prepare their forces . It was a trick to win time while Edigu ' s reinforcements arrived . Vytautas planned to build a great wagon - fort , to stop charging horsemen , and then to destroy them with cannons and artillery . Vytautas ' army was well - equipped , but smaller in number . However , Temur Qutlugh feigned a retreat ( a tried and tested Tatar tactic ) and Vytautas left his wagon fort to pursue him . Once Lithuanian forces were suitably far away from the wagon fort , the units of Edigu appeared from behind and surrounded the Lithuanian army . At this point Tokhtamysh decided the battle was lost and fled the battle with his men . The Tartars then used their own artillery to destroy the Lithuanian cavalry whilst simultaneously capturing the Lithuanians ' wagon fort . Aftermath . Vytautas barely escaped alive , but many princes of his kin ( including his cousins Demetrius I Starszy and Andrei of Polotsk ) and allies ( as for example , Stephen I of Moldavia and two of his brothers ) died in the battle . It is estimated that some 50 dukes fought under Vytautas ' banners and about 20 of them were killed . The victorious Tatars besieged Kiev , but it paid a ransom . The Tatars pillaged as far west as Lutsk , in pursuit of Tokhtamysh , who spent the next seven or eight years in hiding and was assassinated in 1407 or 1408 . Vytautas ' defeat at the Vorskla effectively blocked Lithuanian expansion to southern Ruthenia . His state also lost access to the Black Sea as the Tatars reconquered the southern steppe all the way to Moldavia ; land that was not reclaimed until the Crimean Khanate broke away from the Golden Horde some forty - two years later . After the battle , Yury of Smolensk revolted from Lithuania and Smolensk was not recaptured for five years . Veliky Novgorod and Pskov also rebelled against Lithuanian rule drawing Vytautas into a war with the Grand Duchy of Moscow . Vytautas was forced to abandon his plans to break the Union of Kreva and to ally himself once again with his cousin and King of Poland Jogaila . The Polish – Lithuanian union was reaffirmed in the Union of Vilnius and Radom . Vytautas also turned his plans from expansion southwards to east ( against Moscow ) and west ( against the Teutonic Knights ) . It is suggested that Vytautas learned the staged retreat tactic during the battle and successfully used it himself in the Battle of Grunwald ( 1410 ) , one of the largest battles in medieval Europe and important defeat of the Teutonic Knights .