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He started out in junior hockey with the Kitchener Empires of the Ontario Hockey Association in 1932-33. Hiller went on to play more junior with the Sudbury Cub Wolves in the next two years and senior with the Sudbury Tigers and the Sudbury Falcons, winning the Allan Cup in 1935-36.
After a year in Great Britain with the Harringay Greyhounds, Hiller was signed by the New York Rangers. He played one season for their farm team the New York Rovers and then joined the NHL team. He won the Stanley Cup in 1940.
After 1946 he played with the Pittsburgh Hornets and the Kitchener Dutchmen. He retired as a player in 1948. Hiller spent two seasons as coach of the Los Angeles Monarchs of the Pacific Coast Hockey League (1948-49 and 1949-50).
In the NHL he played 383 games and scored 91 goals and 113 assists. In the playoffs he played in 48 games with 9 goals and 8 assists.