The battle near Oszmiana (modern-day Ashmyany) marked a pivotal moment in the Lithuanian Civil War, a power struggle that erupted following the death of Grand Duke Vytautas the Great. Švitrigaila, vying for sovereignty, aligned himself with forces seeking to end the dominance of Sigismund Kęstutaitis, a contender for the Grand Duchy’s control. The conflict erupted largely due to competing claims from the noble factions, exacerbated by the political landscape of the region, which was characterized by fragmented allegiances and external pressures. As the battle unfolded, both sides employed a mix of military strategies that showcased the evolving nature of warfare in the 15th century, with cavalry charges and archery playing crucial roles.

The engagement involved hundreds of soldiers, highlighting the scale of the confrontation. Each faction sought to not only secure territorial advantage but also the loyalty of various Lithuanian nobles and local populations. The outcome of the battle would influence subsequent military engagements and the broader trajectory of Lithuania’s governance. Following this encounter, hostilities intensified, with both Švitrigaila and Sigismund rallying their supporters to solidify their claims through further skirmishes and alliances.

This initial clash near Oszmiana set in motion a series of battles that would not only reshape the political landscape of Lithuania but also alter relationships with neighboring states, including the Teutonic Order, which was closely watching the developments. The struggle between Švitrigaila and Sigismund was emblematic of the internal conflicts that plagued the Grand Duchy, presenting a microcosm of the challenges faced by ruling dynasties in Central and Eastern Europe during this turbulent period.