Although they have never qualified for the finals of a major tournament, Estonia did compete at the 1924 Olympic Games in Paris.

However, it proved to be a short competition for the side, with their one and only match resulting in a 1-0 defeat to the United States at the Stade Pershing Stadium in the Bois de Vincennes area of the French capital in front of a crowd of over 8,000 fans.

Coached by Hungarian Ferenc Kónya, a former striker who enjoyed a nomadic playing career during the 1920's and 1930's that took him to clubs in Germany, Italy, Switzerland and France, Estonia conceded a penalty after 15 minutes and Andy Straden duly converted from the spot. Estonia had the opportunity to equalise when they were awarded a penalty of their own on 68 minutes, but midfielder Elmar Kaljot hit the bar with his effort and his side would find themselves exiting the competition after just 90 minutes. The United States were then comfortably defeated 3-0 by eventual winners Uruguay in the next round.

However, Estonia decided to remain in Paris for the duration of the competition despite their early elimination, and played a friendly international against Ireland that resulted in a 3-1 loss. The side then toured Germany to play a series of matches against various clubs before returning home. Success would follow for the team five years later as they won the Baltic Cup for the first time in 1929, drawing 2-2 with Latvia before defeating Lithuania 5-2 in the decisive final match of the competition.

For many of the Estonian squad of that era, competing at the Olympic Games proved to be the highlight of their careers, but there are many other stories connected with the players who represented their country in Paris. Striker Johannes Brenner retired from football at the age of 24 to concentrate on his military career, while winger Ernst Joll worked as sports reporter and editor throughout the 1920's. Goalkeeper Evald Tipner would also represent Estonia in hockey during that same Olympic year.

However, there were also plenty of harrowing tales to emerge from the squad during the 1940's, as Hugo Väli, Voldemar Rõks and Heinrich Paal all died at a Soviet Prison camp during the Second World War. In addition, Otto Silber, Harald Kaarmann and Eduard Eelma were all arrested by the People's Commissariat of Internal Affairs (NKVD), sentenced to death and subsequently executed. It was sad end to the story of Estonia's first football heroes.

Estonia squad - 1924 Olympic Games: J.Brenner, E. Einmann, Eduard Ellman-Eelma, V.Gerassimov, N.Javorski, Ernst Joll, Alfei Jürgenson, Harald Kaarmann, Elmar Kaljot, J.Kihlefeld, August Lass, J.Lello, Ralf Liivar, Heinrich Paal, Arnold Pihlak, H.Põder, Bernhard Rein, Voldemar Rõks, Otto Silber, Evald Tipner, Oskar Üpraus, Hugo Väli.

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