Winsor was a star player for Harvard for 2 seasons. He helped the team finish the 1901 season with an undefeated record, including a 4-0 defeat of Intercollegiate champion Yale. He served as team captain as a senior and led the Crimson with at least 18 goals in 10 games. The only losses for the team on the season were to Yale, who won their 4th straight championship as a result.
Winsor returned to the team in 1903 as the program's first head coach and led the team for the next 14 years. In that time Harvard never finished lower than second best and won 6 Intercollegiate championships outright. Winsor developed a defensive system that so effective it was able to shut down Hobey Baker on multiple occasions. He also was the first to use a platoon system, rotating all positions on the team when there was a stoppage in play rather than have most players remain on the ice for the entire game (the common practice of the day).
Winsor later coach the US national team to a silver medal at the 1932 Olympics. He is also a member of the US Hockey Hall of Fame.
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