 Waterfield attended Van Nuys High School where he was a star football player.Waterfield enrolled at the University of California, Los Angeles (UCLA) where he played college football for UCLA Bruins football in 1941, 1942, and 1944.During the 1942 regular season, he led the Pacific Coast Conference in passing, completing 53 of 125 passes for 1,033 yards and 12 touchdowns.