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The club was founded as the Brandon Hockey Club in 1898. The club first fielded teams in the intermediate division of the Manitoba & Northwestern Hockey Association. In 1902, the club started fielding teams in the senior division. In 1904, the senior team made its first challenge for the Stanley Cup, in 1904 against the Ottawa Hockey Club (the Silver Seven). In 1906, the club fielded its first professional senior team, which challenged for the Stanley Cup in 1907 in the MPHL playoff against the Kenora Thistles. The professional league folded after a few seasons, but the Wheat City club continued fielding senior-level amateur teams until 1935. The club challenged for the Allan Cup national senior championship in 1921.
Canadian Amateur Hockey Association (CAHA) president H. J. Sterling chose Winnipeg as the host location for the 1921 finals at an arena with an artificial ice surface. The Manitoba Amateur Hockey Association and the Brandon Wheat City Hockey Club wanted to have the games played at the rink in Brandon, and contested that Sterling was incorrect to make the decision himself without consulting the CAHA executive. They sought an injunction against Sterling to prevent the games from being played in Winnipeg, but were denied when the justice declined to interfere in CAHA business. The Toronto Varsity Blues men's ice hockey defeated the Brandon Wheat City Hockey Club in the finals for the Allan Cup.