Randall had a long and varied playing career at a time when the professional ice hockey world was changing. He was an accomplished scorer when playing forward, and was a good defencemen which he became exclusively later in his career. He turned professional in the Ontario Professional Hockey League (OPHL), and played in the Maritime Professional Hockey League, the Eastern Ontario Professional Hockey League and the Saskatchewan Professional Hockey League before joining the Toronto Blueshirts of the National Hockey Association (NHA) in 1915. He played for the organization until 1923, as it changed from the Blueshirts to Arenas to St. Patricks, winning two Stanley Cups, in 1918 and 1922. In 1923, he joined the Hamilton Tigers, which in 1924 became embroiled in a labor conflict and his contract was sold to the new New York Americans, for which he played two years before becoming a player coach with the Providence Reds. He became a full-time coach in 1928, but still had some playing time left in him, playing for the Oshawa Patricias when the OPHL was revived in 1930.
