Crawford started out in senior hockey in Montreal in 1907-08 before moving out to Saskatchewan to play from 1909-10 to 1911-12. He helped lead the Bulldogs to a Stanley Cup victory in 1912–13 (prior to the formation of the NHL). He won his second Stanley Cup as a member of the 1917–18 Toronto Arenas. Crawford then played with the senior Saskatoon Crescents for two seasons before playing four seasons in the Western Canada Hockey League. Crawford then finished off his career with four seasons with the Minneapolis Millers of the American Hockey Association. He retired in 1930.