Masterson was a player-coach during his last two seasons in Washington and with the
New York Yankees. In 1947, he was hired to coach
University of Toronto's
Varsity Blues football team. He was an assistant coach for one season to learn
Canadian football, then took over as head coach the following year. In eight seasons, he compiled a 45-21-6 record and won the
Yates Cup three times (1948, 1951, 1954). He was also the head men's basketball coach from 1947 to 1955 and amassed a 38–24 record. ==Executive==