An outstanding athlete, Winslow was a three-year letterman in both lacrosse and soccer. He was a unanimous All-America first team pick in 1933 and helped the lacrosse team to an overall record of 6-1-1. Cornell's head lacrosse coach, Nicky Bawlf, considered Winslow as one of the greatest lacrosse players ever developed in college. He was also an honorable mention All-American at wing attack in 1932. Winslow was chosen to represent the United States as a member of the U.S. Lacrosse team while in his junior year at Rochester Medical School. He was a halfback in soccer and captained the team in 1932.
