In the 19th century, organized sport was centred around the clubs of Montreal. For many members of Montreal society, sport was a social occasion as much as an athletic one. And, athletes of the day rarely specialized in one particular sport, enjoying companionship and competition in a variety of pastimes. Hartland MacDougall was emblematic of these traditions. He came by them honestly as his father was a member of one of Canada's oldest sport clubs, the Montreal Snowshoe Club, where he won the General Sir Frederick Williams' Cup race in 1861. The younger MacDougall excelled in many different sports. A decade after his birth, he was remembered by Andy O'Brien of the Montreal Star as "second only to Lionel Conacher" as a "national all-time, all-round athlete". Like Conacher, MacDougall was an accomplished hockey player. He played on the Montreal Victorias hockey club from 1894 to 1898. During the fledgling years of organized amateur hockey, the Victorias were an early Stanley Cup powerhouse and the young MacDougall played an increasingly prominent role. Although his brother, Robert, was a star forward for the Victorias, MacDougall played primarily as a substitute, first in goal and then on defense. In 1898, his final season with the club, MacDougall played all eight games for the undefeated Victorias and scored three goals. He was a member of the Victorias teams that won the Stanley Cup in 1895, 1896, 1897, and 1898. MacDougall was a star fullback with the football clubs of the Montreal Amateur Athletic Association in the 1890s. He was also active with the Montreal Hunt and Racket clubs. But in the later years of his athletic career, MacDougall was well known as a polo player. He founded the Back River Polo Club, which later became the Montreal Polo Club. In 1910, famed English player, Arthur Grenfell, donated the Grenfell Polo Challenge Cup to be awarded for the Canadian championship. While the Cup evolved into primarily an Eastern Canadian championship, MacDougall led the Back River Polo Club to the Grenfell Cup in 1911 and 1914. When the competition resumed following the First World War, the MacDougall-led Montreal Polo Club dominated the competition, winning every year from 1920 to MacDougall's final year of 1928 (except for 1925). Continuing the family sporting tradition, MacDougall was joined by his son Hartland C. MacDougall for his final three Grenfell Cups. A stroke in the late-1920s ended MacDougall's playing days, but did nothing to diminish his interest in sport. As a financier, he participated in the creation of the Montreal Forum and was a director with the Canadian Arena Company, which operated the building. As well, he helped found the Montreal Maroons hockey team in 1924, for which the Forum was built. Until his final days, MacDougall was a regular at the Montreal Forum for both junior and NHL games.