Estonia
A pre-selection round in place before the contest in 1993 sorted the Estonian entry out, and as such the country had to wait until 1994 to get its debut. Silvi Vrait represented the country, but failed to reach the final. Whether or not it was due to the result, Estonia didn't take part in 1995, but since 96' they have been a steady Eurovision participant.
Since the introduction of semi-finals in 2004, Estonia has failed to reach the final a total of nine times. But before that, the country had already won once, in 2001 where Tanel Padar and Dave Benton made most of Europe clap and sing a long to Everybody.
In 2015, Elina Born & Stig Rästa finished 7th at the contest, but they were followed up by two entries that didn't reach the final.