Bowie played centre and rover for numerous amateur Montreal teams in the 1890s as a teenager, and for the Montreal Victorias of the CAHL and the ECAHA from the 1896 to the 1908 seasons. He was a five-time scoring champion and scored an unprecedented 234 goals in 80 recorded league games. Bowie played for the Vics' final Stanley Cup champion club in 1898. An accomplished stickhandler who credited his skill to employing an unusually short stick, he was cited in many all-star lists as one of the very best forwards of hockey's first half-century.
On February 20, 1901, Bowie of the Montreal Victorias scored seven goals in a game and was well positioned to dominate the CAHL, and two weeks later, he scored 6 goals against the Montreal Shamrocks. He finished the season with 24 goals, 14 more than his nearest rival. Over his career, Mr. Bowie would average almost three goals per game, a mark only matched by Frank McGee in major senior play.
Bowie never accepted money to play hockey, famously refusing all importuning and turning down large offers, and was quoted as saying, "I am an amateur, was an amateur, and will die an amateur." He weathered a scandal in 1907 where it was alleged that he had taken pay from the professional Montreal Wanderers club, but the allegations were proven baseless -- although the Wanderers did send him a grand piano in anticipation of Bowie's acceptance of their offer, an inducement he refused to receive. He did play against professionals in the ECAHA and IPHL.
Bowie retired from major play in 1909 - along with Harvey Pulford, Harry Westwick and Alf Smith, one of the final players who had played in the 19th century - when the professional National Hockey Association formed and the Victorias faded from major hockey prominence. He skated ten games for the Vics in the next two seasons in lower level amateur competition, but his retirement was punctuated by an injury in 1910. He became a referee in retirement, officiating for the NHA thereafter.
He was one of the original inductees of the Hockey Hall of Fame when it was formed in 1945.