The Wanderers' first Stanley Cup challenge was played against the Ottawa Hockey Club on March 2, 1904, resulting in a 5–5 tie game.

Ottawa and the Wanderers would meet again in 1906, after a regular season tie for first place in the Eastern Canada Amateur Hockey Association (ECAHA), and played a two-game, total-goals series for the league championship and the Stanley Cup.

The Wanderers won their third consecutive league title in 1907–08, while defending the Stanley Cup in a mid-season challenge by the Ottawa Victorias in January.

After the 1907–08 regular season, Montreal defended the Stanley Cup twice in March 1908, in challenges by the Winnipeg Maple Leafs, and the Toronto Professional Hockey Club.

The team included five future honoured members of the Hockey Hall of Fame – Moose Johnson, Hod Stuart, Riley Hern, Lester Patrick, and Ernie Russell.

Before the 1909 season started, Montreal defended the Stanley Cup in a challenge by the Edmonton Hockey Club, winning 13–10 in two games.

[4] This upset the other members of the Eastern Canada Hockey Association (ECHA), who would receive a smaller share of the proceeds from games played in the Wanderers rink.

Doran sold the club to Eddie McCafferty, the secretary of the Montreal Royals minor league baseball team, owned by Sam Lichtenhein.

The Wanderers successfully defended the Stanley Cup for the final time versus the Berlin Dutchmen in March 1910.

Montreal's last winning season came in 1914–15, when they tied for first place and lost in a playoff series for the league championship.

Before the fire, they had successfully obtained goaltender Hap Holmes from the Seattle Metropolitans of the Pacific Coast Hockey Association (PCHA) and it seemed that they might turn around their misfortunes.

The Maroons, too, would eventually suspend operations in 1938, ending efforts to entrench separate Montreal-based teams for French- and English-speaking fans.

The Wanderers won or defended the Cup 10 times in their first seven years of existence, and lost only two direct challenges (to Ottawa in March 1904, and to Kenora in January 1907) during that period.