In 1972, the Saint Louis Stars of the North American Soccer League () selected Winter as their goalkeeper. That year, he had the second lowest goals against average (Gaelic Athletic Association) in the league, behind Kenny Cooper. Winter spent the next two years with the Stars before the Chicago Sting selected him in the 1975 Expansion Draft.
He played one season with the Sting, then left the
In 1972, Winter earned his first cap with the United States. national team
He never became a regular starter for the national team as he had significant competition in the nets from Mike Ivanow and Bob Rigby. However he did earn six caps, but had no shutouts, and more significantly, no wins.