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After the decline of the Teutonic Order following its defeat in the Battle of Grunwald in 1410, and the defeat of the Livonian Order in the Battle of Swienta on 1 September 1435, the Livonian Confederation Agreement was signed on 4 December 1435. The Livonian Confederation ceased to exist during the Livonian War (1558–82). The wars had reduced the Estonian population from about 250–300,000 people before the Livonian War to 120–140,000 in the 1620s. The Grand Duchy of Moscow and Tsardom of Russia also attempted invasions in 1481 and 1558, both of which were unsuccessful .

When did the Battle of Grunwald take place?
1410