He started out in junior hockey with the St Michaels College, winning the Memorial Cup in 1934. In 1935-36 Crawford switched to the West Toronto Nationals where he won a second Memorial Cup. Crawford started his National Hockey League career with the Boston Bruins in 1938. He would also play his entire career with the Bruins and retired after the 1950 season. In 1943 and 1946, he was a member of the NHL All-Star Team. He would win two Stanley Cups with Boston 1939, 1941. In 1950 he joined the Hershey Bears as a player-coach for two years. He retired as a player in 1952.