At the 2018 Junior World Championships in Davos, Switzerland, Winters won the bronze medal in the Super-G, was ninth in the Downhill, and 22nd in the Alpine Combined. In November 2018, he made his World Cup debut in the slalom at Levi, Finland. The following March, he gained his first national championship title, winning the alpine combined at Sugarloaf, Maine. He followed that up with his second national title, in slalom at Waterville Valley.