Windingstad took part in FIS races from November 2008 . He achieved his first rankings in the front field in spring 2011. After he had to pause the entire 2011/12 season due to injury, he achieved his first victories in this racing category in the winter of 2012/13. At the end of November 2013, he began to take part in European Cup races. In his third appearance, on December 3, 2013 in the giant slalom in Klövsjö / Vemdalen , he was among the top ten. After two more top 10 placements, he made his World Cup debut on February 2, 2014 , with re eliminated in the giant slalom in St. Moritz in the first round. In the further course of the winter 2013/14 he took part in the Junior World Championship in Jasná and won the bronze medal in the giant slalom there.
On March 11, 2014, Windingstad stood third in the giant slalom in Soldeu for the first time on a European Cup podium and on December 18, 2014 he won his first race in this racing series in Pozza di Fassa in the same discipline. He scored his first World Cup points on December 6, 2015, finishing 28th in the giant slalom on the Gran Risa in Alta Badia . Despite two further results in the points shortly afterwards, he was only used in the European Cup for the rest of the winter 2015/16. He achieved another podium place. In the 2016/17 season Windingstad finished in the points only once in the World Cup. In the European Cup, however, he reached four podium places, including a victory in the giant slalom in Jasná.
After a subdued start to the 2017/18 season, Windingstad made it into the top 10 of a World Cup race for the first time on March 3, 2018, finishing 8th in the giant slalom in Kranjska Gora . He confirmed his upward trend in the 2018/19 World Cup season with three further top 10 placements. After two seventh places in the subsequent races in Bansko , he achieved his first World Cup podium finish on March 9, 2019 with second place in the giant slalom in Kranjska Gora. He achieved his first World Cup victory on December 23, 2019 in the parallel giant slalom in Alta Badia , where he prevailed against the German Stefan Luitz in the final .
Norway
