Sildaru won a gold medal in the slopestyle event in the 2016 Winter X Games beating Tiril Sjåstad Christiansen. 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 and 2016Dew Tour.
During the Big Air competition of the 2017 Winter X Games Norway, Sildaru became the first woman to ever land a Switch 1260° Mute and a 1440° during a competition.
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.