Estonia entered the Eurovision Song Contest 1999, held in Jerusalem, Israel. This was their fifth entry at Eurovision, having debuted at the 1994 contest.

The Estonian representative for the contest was Evelin Samuel and Imbi Rätsep (also known as "Camille") with the song "Diamond of Night". It was the first contest with non-Estonian songs in the national final and the first time a non-Estonian song was picked to represent Estonia.

The Estonian National final was held on January 30, 1999 at the ETV Studios in Tallinn. It was hosted by Romi Erlach and Marko Reikop.

The format of the final was the same as in previous years, with a jury of judges awarding points to their favourite songs from the 10 in the final. The jury of 10 international judges included 1997 Eurovision winner Katrina Leskanich, Bjorgvin Halldorsson, conductors Anders Berglund, Noel Kelehan, Nana Mouskouri and Kobi Oshrat.

Samuel and Rätsep performed last of 23 countries, succeeding the entry from Bosnia and Herzegovina. At the close of the voting it had received 90 points, placing 6th.

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