Estonia first entered the Eurovision Song Contest 1994 along with Poland. Its first appearance would have taken place in 1993 with Janika Sillamaa and "Muretut meelt ja südametuld", however, a qualification round was just installed for former Eastern Bloc countries and she did not manage to qualify for the Grand Final.
Its first contest participation in 1994 was not a successful one, coming second last only to Lithuania. As such, the country was relegated from the 1995 contest. Its second entry, Maarja and Ivo Linna with Kaelakee hääl, in 1996 was the complete opposite, coming 5th with 94 points. This was the first time a former USSR country placed in the top 5.
In 2001, Tanel Padar, Dave Benton and 2XL gave the country its first win with the song "Everybody", making Estonia the first ex-USSR country to win the Contest and the second country in the former Eastern bloc after Yugoslavia. At 50 years old, Benton became the oldest person to win the contest.
Since the introduction of the semi-finals in 2004, the country has placed in the top 10 five times, in 2009, 2012, 2015, 2018 and 2023. Their total of eleven top 10 placings is more than Latvia (4) and Lithuania (3).
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- The country is one of four to have selected all of their entries via a national final, the others being Albania, Denmark and Finland.