Sildaru won a gold medal in the slopestyle event in the 2016 Winter X Games beating Tiril Sjåstad Christiansen.[2] With this win, at age 13, Sildaru became the youngest gold medalist to date at a Winter X Games event and the first person to win a Winter X Games medal for Estonia. She is also the youngest to win two X Games gold medals. Sildaru has won the women's slopestyle on the 2015[3] and 2016[4]Dew Tour.
During the Big Air competition of the 2017 Winter X Games Norway, Sildaru became the first woman ever to land a Switch 1260 ° Mute and a 1440° during a competition.[5] Because of her young age, the first World Cup event she was allowed to participate in was on 27 August 2017 in Cardrona, New Zealand. She won the slopestyle competition.[6]
Despite being the gold medal favorite for the women’s slopestyle event in 2018 Winter Olympics, she missed competing in the Games because of a knee injury.[7] However she later recovered and was able to compete in the world championships winning gold in halfpipe.[8] In the 2020 Youth Olympic Games she won a gold medal for the Women's Freestyle Skiing.[9]