The Battle of the Vorskla River was fought on August 12, 1399, between the Tatars of the Golden Horde, under Edigu and Temür Qutlugh, and the armies of Tokhtamysh and a large Crusader force led by Grand Duke Vytautas the Great of Lithuania.

[3] 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 suzerainty over Ruthenian lands.

[6] Once the two armies met, Temur Qutlugh proposed a three-day ceasefire to allow both sides to prepare their forces.

[10] However, Temur Qutlugh feigned a retreat (a tried and tested Tatar tactic) and Vytautas left his wagon fort to pursue him.

[12] 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.

His state also lost access to the Black Sea as the Tatars reconquered the southern steppe all the way to the borders of Moldavia;[13] lands that were held by the Golden Horde until the Crimean Khanate broke away from its rule some forty-two years later.

Veliky Novgorod and Pskov also rebelled against Lithuanian rule, drawing Vytautas into a war with the Grand Duchy of Moscow.

[6] 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.