The Livonian War of 1558–1583 was a lengthy series of wars between the Tsardom of Russia and a variable coalition of Denmark–Norway, Grand Duchy of Lithuania, the Kingdom of Poland (later the Polish-Lithuanian Commonwealth), and Sweden for control of medieval Livonia, the territory of the present-day Estonia and Latvia.

By the late 1550s, the Reformation and Counter-Reformation had caused internal conflicts in the Livonian Confederation, while its Eastern neighbour Russia had grown stronger after annexing the khanates of Kazan (1552) and Astrakhan (1556). The conflict between Russia and the Western powers was exacerbated by Russia's isolation from sea trade. Nor could the tsar hire qualified labour in Europe.

In 1547, Hans Schlitte, the agent of Tsar Ivan IV, employed handicraftsmen in Germany for work in Russia. However all these handicraftsmen were arrested in Lübeck at the request of Livonia. The German Hanseatic League ignored the new Ivangorod port built by tsar Ivan on the eastern shore of the Narva River in 1550 and continued to trade with the ports owned by Livonia.

Tsar Ivan IV demanded that the Livonian Confederation pay 40,000 talers for the Bishopric of Dorpat, based on a claim that the territory had once been owned by the Russian Novgorod Republic. The dispute ended with a Russian invasion in 1558. Russian troops occupied Dorpat (Tartu) and Narva, laying siege to Reval (Tallinn). The goal of Tsar Ivan was to gain vital access to the Baltic Sea.
Tsar Ivan's actions conflicted with the interests of other countries. In the wake of the disastrous Battle of Ergeme, the weakened Order of Livonia was dissolved (Wilno Pact, 1560), while the order assigned its lands (Livonia) to Lithuania united with Poland. The last Master of the Order of Livonia, Gotthard Kettler, became the first ruler of the Polish and Lithuanian (later the Polish-Lithuanian Commonwealth) vassal state Duchy of Courland.

The city council of Reval turned to King Eric XIV of Sweden for help against other troops. In 1561, Swedish forces arrived and the noble corporations of Harria–Vironia (Harju–Viru) and Jervia (Järva) yielded to Sweden, forming the Duchy of Estonia.
Frederick II of Denmark sent troops to protect the western Estonian territories he had recently bought from the bishop of Ösel–Wiek. By 1562, Russia found itself in wars with Lithuania and Sweden. In the beginning, the Tsar's armies scored several successes, taking Polotsk (1563) and Pernau (Pärnu) (1575), and overrunning much of Lithuania up to Vilnius, which led him to reject peace proposals from his enemies.
However, the Tsar found himself in a difficult position by 1579. The Crimean Tatars devastated Russian territories and burnt down Moscow (see Russo-Crimean Wars), the drought and epidemics have fatally affected the economy, and Oprichnina had thoroughly disrupted the government, while Lithuania had united with Poland (new union in 1569) and acquired an energetic leader, king Stefan Batory. In the Polish–Muscovite War (1577–1582), not only did Batory reconquer Polotsk (1579), but he also seized Russian fortresses at Sokol, Velizh, Usvzat, Velikie Luki (1580), and laid siege to Pskov (1581–82). Polish-Lithuanian cavalry devastated the huge regions of Smolensk, Chernigov, Ryazan, southwest of the Novgorodian territory and even reached the Tsar's residences in Staritsa. Ivan prepared to fight, but Poles retreated. In 1581, a mercenary army hired by Sweden and commanded by Pontus de la Gardie captured the strategic city of Narva and massacred its inhabitants, 7,000 people .

These developments led to the signing of the peace Treaty of Jam Zapolski in 1582 between Russia and the Polish-Lithuanian Commonwealth in which Russia renounced its claims to Livonia. The Jesuit papal legate Antonio Possevino was involved in negotiating that treaty. The following year, the Tsar also made peace with Sweden, relinquishing most of Ingria. The situation was reversed 12 years later, according to the Treaty of Tyavzino which concluded a new war between Sweden and Russia.