The first attempts to regulate competitive ice hockey matches came in the late 1880s. Before then, teams competed in tournaments and infrequent challenge contests that prevailed in the Canadian sports world at the time. In 1887, four clubs from Montreal, the Montreals, the Crystals, the Victorias, McGill University, as well as Ottawa HC formed the Amateur Hockey Association of Canada (AHAC) and developed a structured schedule. Lord Stanley donated the Stanley Cup and appointed Sheriff John Sweetland and Philip Dansken Ross as its trustees; they chose to award it to the best team in the AHAC, or to any pre-approved team that won it in a challenge. Since the Cup carried an air of nobility, its prestige greatly benefited the AHAC.
The coordination and regularized schedule that the AHAC brought helped commercialize amateur ice hockey, which ran against the spirit of the prevailing amateur ethic. As the importance of winning grew, AHAC clubs began recruiting players from outside, and the disparity in skill between teams of the AHAC and those of other leagues became clearer. Since team owners in the AHAC wanted to defend the Stanley Cup and maintain the organization's honour, and rink owners wanted senior hockey as their marquee attraction, AHAC clubs became increasingly reluctant about admitting new teams into the league and the senior series. When the relatively weak Ottawa Capitals joined in 1898, the five original clubs withdrew from the AHAC to form the new Canadian Amateur Hockey League (CAHL). In 1903, four new teams created the Federal Amateur Hockey League (FAHL), and in 1904, the International Hockey League (IHL), based around Lake Michigan, was created as the first fully professional league. In recruiting players, the IHL caused an "Athletic War" that drained amateur clubs of top players, most noticeably in the Ontario Hockey Association (OHA).
By the 1905–06 season, several of the FAHL and CAHL markets were overcrowded; for example, Montreal had seven clubs. To solve the problem, the leagues merged into the new Eastern Canada Amateur Hockey Association (ECAHA), which kept four of the Montreal clubs. The new league mixed paid and amateur players in its rosters, which led to the demise of the IHL. With the IHL gone, teams from Toronto, Berlin (now Kitchener), Brantford, and Guelph filled the void with the Ontario Professional Hockey League (OPHL). Bidding wars for players led many ECAHA teams to lose money, and before the 1907–08 season, the Montreal Victorias and the Montreal HC left. The ECAHA dropped "Amateur" from its name for the 1909 season, and on November 25, it folded. Ottawa HC, Quebec HC, and the Montreal Shamrocks founded the Canadian Hockey Association (CHA), and the league later admitted the Montreal Le National and All-Montreal HC. Rejected CHA applicants formed the National Hockey Association (NHA).
When compared to the CHA, the geographical distances between NHA teams were much greater; however, the NHA's financial backers were more notable businessmen. These businessmen applied financial principles similar to those of early baseball, and the leagues quickly entered a bitter bidding war over players. In particular, after being rejected from the CHA, Renfrew aggressively pursued any players that the CHA's Ottawa club wanted. Montreal became a notable battleground as the NHA established two franchises, including the modern-day Montreal Canadiens. With its significantly wealthier backers, the NHA easily recruited the top players, leaving the CHA teams, except Ottawa, relatively mediocre. Ottawa regularly trounced its opponents, and league attendance and interest dropped. The CHA's final season lasted eight games, and the league folded in 1910 as its Ottawa and Montreal clubs joined the NHA.