After Estonia came under the control of the Teutonic and Livonian Orders in the early 14th century, the region remained a battleground for dominance over the Baltic. This set the stage for the Livonian War (1558–1583), a conflict that reshaped the region's political landscape. The war was fought between Russia, under Tsar Ivan IV, and a shifting coalition of Denmark-Norway, Sweden, and Poland-Lithuania, all seeking control of Livonia, which included modern-day Estonia and Latvia.
Russia initially dominated the war, seizing key Estonian cities such as Narva and Tartu in the late 1550s. The Livonian Confederation, weakened by internal divisions and lacking strong defenses, quickly fell apart. As Russia pushed west, Poland-Lithuania, Denmark, and Sweden intervened, each seeking their own share of the territory.
By 1561, Sweden established control over northern Estonia, creating Swedish Estonia, while Denmark acquired the Bishopric of Ă–sel-Wiek. The Teutonic Order's remnants, led by Gotthard Kettler, secularized and created the Duchy of Courland under Polish-Lithuanian protection. Sweden, meanwhile, solidified its grip on Estonia despite repeated Russian invasions.
The tide of the war turned in the late 1570s when Polish-Lithuanian King Stephen Báthory launched successful counterattacks, culminating in the Siege of Pskov (1581). The conflict ended with the Truce of Jam Zapolski in 1582, which forced Russia to relinquish its Livonian conquests to Poland-Lithuania. The following year, the Truce of Plussa between Sweden and Russia secured Swedish control over northern Estonia, further cementing Swedish dominance in the region.
Estonia's incorporation into the Swedish Empire marked the end of the Teutonic and Livonian Orders’ influence. The Livonian War set the stage for Swedish Estonia, which would last until the early 18th century when Estonia fell under Russian control during the Great Northern War.