The Livonian War of 1558-1583 was a lengthy military conflict between Russia and its western neighbours for control of present-day Estonia and Latvia, formerly known as Greater Livonia.

By the late 1550s, the Livonian Confederation had been weakened by the Reformation, while its Eastern neighbor Muscovy had grown stronger after defeating the Muslim khanates of Kazan and Astrakhan.

The Russian tsar Ivan IV demanded that Livonian Confederation pay huge taxes (40,000 talers) for the Bishopric of Dorpat. The dispute ended with a Russian invasion in 1558. Russian troops occupied Dorpat and Narva, laying siege to Reval. The goal of the Russian tsar was to gain vital access to the Baltic Sea.

That went against the interests of other countries. In 1561, the weakened Order of Livonia was dissolved, while its lands were assigned to Poland (Courland), Sweden (Estland), and Denmark (Ösel). The last Master of the Order of Livonia, Gotthard Kettler, became the first ruler of the Polish vassal state Duchy of Courland.

Erik XIV of Sweden and Frederick II of Denmark sent troops to protect their newly-acquired territories. In 1561, the city council of Reval in Estonia surrendered to Sweden. Reval became the outpost for further Swedish conquests in the East Baltics. By 1562, Russia found itself in wars with the kingdoms of Poland and Sweden. The tsar's armies were initially successful, taking Polotsk (1563) and Pernau (1575) and overrunning much of Lithuania up to Vilnius.

Having rejected peace proposals from its enemies, the tsar found himself in a difficult position by 1579, when the Oprichnina had thoroughly disrupted the Russian economy, while Lithuania had united with Poland (1569) and acquired an energetic leader, Stefan Batory (1576). Not only did Bathory reconquer Polotsk, but he also laid siege to Pskov (1579). In 1581, a mercenary army of Sweden under Pontus de la Gardie captured the strategic city of Narva.

Finally, in 1582, the peace Treaty of Jam Zapolski was signed between Russia and Poland with Russia renouncing its claims to Livonia. The following year, the tsar also made peace with Sweden. Under the Treaty of Plussa, Russia lost Narva and the southern coast of the Gulf of Finland, being its only access to the Baltic Sea. The situation was reversed 12 years later, according to the Treaty of Tyavzino.