1903-1909: 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.

1909/10: With the rise of professional hockey, it would be decided that the Eastern Canadian Amateur Hockey Association would dissolve and reform into the Canadian Hockey Association, the first major professional hockey league in Canada. Because the other owners weren’t big fans of Wanderer owner/player Jimmy Gardner, they decided to exclude the Wanderers from the new league. Incensed Gardner decided to form a rival league of his, which he vowed would run the CHA out of business. Hooking up with Ambrose O’Brien, a millionaire who had a reputation for having more money, then he knew what to do with, Gardner set about forming the NHA (National Hockey Association), which began play in January 1910. Within a month, the weaker poorly run CHA went out of business and merged into the NHA, giving Jimmy Gardner the last laugh. The Wanderers would dominate the NHA posting an 11-1 record while scoring an incredible 91 goals, led by Ernie Russell, who put the puck in the net 32 times in just 12 games. By winning the NHA Championship known as the O’Brien trophy, the Wanderers would go on to reclaim the Stanley Cup. The OPHL Champion Berlin Dutchman would challenge them. However, in a one-game showdown, the Wanderers would win easily 7-3.

1910/11: The Wanders who had been holders of the Stanley Cup for the better part of five years began to show their age as they finished in fourth place with a disappointing record of 7-9. Along the way, Jimmy Gardiner would depart selling the team to Sam Lichtenstein. However, Cleghorn would endear himself to Montreal fans with his fast end-to-end rushes as well as his tough defensive play in his first season with the Wanderers.

1911/12: Despite a solid season from Ernie Russell who scored 27 goals, Art Ross, who scored 16, and Odie Cleghorn, who scored 23, the Wanderers continued to play lackluster hockey finishing third in a four-team league with a 9-9 record.

1912/13: Harry Hyland returns after a stint in the PCHA with the Westminster Royals scoring 27 goals. However, the Wanderers would fall 12 points shy of first place while finishing in second place with a 10-10 record.

1913/14: The Wanderers would struggle all season finishing in fifth place with a lousy record of 7-13, despite solid seasons from Harry Hyland, who scored 30 goals and Sprague Cleghorn, who added 12 of his own while patrolling the blue line.

1914/15: Buoyed by Sprague Cleghorn’s impressive 21 goals, the Wanderers had a solid season posting a 14-6 record to finish in a flat-footed tie for the Ottawa Senators for first place. However, in a two-game total goal series for the right to face the Vancouver Millionaires for the Stanley Cup, the Wanderers would lose 4-1, as both teams swapped shutouts.

1915/16: Injuries would limit Sprague Cleghorn to eight games, while Harry Hyland began to show the effects of age scoring fewer goals than games played for the first time in his career, as the Wanderers struggled finishing in fourth place with a disappointing record of 10-14.

1916/17: The Wanderers start off the season struggling with a terrible 3-7 record. At midseason because of the unethical business practices of Toronto Blueshirts owner Eddie Livingstone, Wanderers owner Sam Lichtenhein rallied the other owners and convinced them to throw Livingstone and his Blueshirts out of the league. This would give the Wanderers a reprieve as the NHA decided to go with a split season. However, the Wanderers continued to sink to lower depths with a 2-8 record, thus finishing the year dead last at 5-15. Things would only get worse as Sprague Cleghorn broke his leg late in the season, as his brother Odie scored an impressive 28 goals, to be the only Wanderers to top 20 goals on the season. Following the season, Eddie Livingstone threatened to sue the owners because they unfairly kicked him out of the NHA. Under the guidance of Sam Lichtenhein as well as Montreal Canadiens owner George Kennedy, the other owners decided to form a new league the following season called the National Hockey League. Livingstone could return to the NHA, but now he would be in a one-team league. Thus the Wanderers, Quebec Bulldogs, Canadiens, and Ottawa Senators went about forming the new NHL. After the Bulldogs had to drop out because of financial concerns, it again was Lichtenhein along with George Kennedy, who worked out a deal. The Arena Gardens of Toronto that would revive the now abandoned Blueshirts and rename them the Toronto Arena, thus sticking it to Livingstone, once again as his team was now in the NHL, with a new name and new ownership.

1917/18: The Wanderers played their first-ever NHL game in Toronto, defeating the Arenas 10-9 on the leagues opening night December 19, 1917. However, the Wanderers were drowning in problems, as they were hard hit financially because of the war. Owner Sam Lichtenhein threatened to withdraw from the league because of the scarcity of good players, due mostly to the outbreak of World War I. Making matters worse the Cleghorn brothers (Odie and Sprague) was unable to play. Sprague was still recovering from his broken leg while Odie couldn’t play due to avoiding military enlistment. Things got so bad that the other teams sent some of their players to the Wanderers to keep them afloat, as the Wanderers lost their next five games. Things would go from bad to worse when a fire destroyed their home at the Westmount Arena. The fire, which started in the Wanderers’ locker room, destroyed all the Wanderers’ equipment. The Montreal Canadiens, who were also using the Westmount Arena that season returned to the Jubilee Rink with an offer to share the building with the Wanderers. Another offer came from the city of Hamilton; however, owner Sam Lichtenhein chose to fold citing he had already lost $30,000. Despite the suspicious nature of the fire, there would be no official investigation for arson as the Wanderers only NHL season ended with a 1-5 record, as the Wanderers players would be distributed around the rest of the league.

1918-1924: After the Wanderers folded Anglo fans in Montreal were left without a team until the NHL decided to expand to six teams with the Montreal Maroons being added to Canada’s largest city.