Founded in 1903 for the Anglo fans of Montreal, the Wanderers intended to wander across Canada for Stanley Cup challenges, hence the name Wanderers. In an era when Montreal was the largest city in Canada, teams were founded for every type of fans the Victorias represented the Scottish, while the Shamrocks represented the Irish.

Eventually, a team named the Canadiens would be founded to represent the French. The Wanderers were an immediate success, nearly taking the Stanley Cup away from the legendary Ottawa Silver Seven, by skating to a 5-5 deadlock on March 2nd.

There would be no Game 2 as the Wanderers, and Silver Seven could not agree on where to play the game. The Wanderers would get another chance two years later as they ended Ottawa's three-year reign by winning a two-game total goal series 12-10.

Over the next three years, the Wanderers led by Lester Patrick, goalie Doc Menard, defensemen Billy Strachan and Rod Kennedy and forwards like Pud Glass, Ernie Russell, and Ernie Johnson would accept seven challenges for the Stanley Cup only losing once in January of 1907 to the Kenora Thistles who had a group of professional ringers led by Art Ross. However, just two months later, the Wanderers will exact revenge traveling to the small Ontario town of Kenora to reclaim the cup.

The Wanderers would hold the cup until 1909, beating back challengers like the Edmonton Eskimos and the Winnipeg Maple Leafs. However, in 1909 they would not even be able to finish in second place in their league as the era of Amateur teams fighting for the Stanley Cup came to an end.