Willing was a member of three Harvard national championship teams and captained the undefeated team of 1932. Part of the “one-two punch” with fellow Hall of Famer Frances Beckman Pool, and defeated his teammate in the finals of the Harvard University Championship. Willing was also a member of the 1932 Harvard tennis team that advanced to the finals of the National Championship against the University of North Carolina. He later became a national squash champion.