Both teams saw success during the Original Six era, with either the Canadiens or Maple Leafs winning the Stanley Cup in 19 out of 25 seasons.

The rivalry's association with larger societal issues in the country has left an imprint on Canadian culture, most notably through the publication of the short story The Hockey Sweater by Roch Carrier.

Although the rivalry is no longer influenced by its historical associations, it remains symbolic of the relationship between the country's two largest cities, Toronto and Montreal.

[1] Although Montreal remained the Province of Canada's largest city throughout that period, Toronto's population also began to grow significantly.

[2] In addition to being economic rivals, Montreal and Toronto's early identities were rooted in the cultural differences between the two cities.

[3] From its foundation, Montreal was historically viewed as Canada's cosmopolitan centre for culture; which contrasted Toronto's pre-World War era reputation as a small city and bastion for "Victorian morality".

[7] The resulting dispute led to the creation of the modern NHL, as well as the present hockey club in Toronto; with the new NHL owners opting to establish a hockey club in Toronto in an effort to maintain a four team circuit that included the Canadiens, Montreal Wanderers, and Ottawa Senators.

Toronto advanced to win the 1918 Stanley Cup Finals, as the two-game NHL Championship series was determined by total goals scored.

[15] An exhibit space had been prepared for the Stanley Cup at the expo's Quebec pavilion, as the heavily favored Canadiens were supposed to beat the Leafs quite handily.

[11] Toronto came close to reaching the Finals in 1993, where they would have faced the Wales Conference champion Canadiens in the 100th anniversary year of the Stanley Cup.

[25] When asked about his refusal to waive, Gorges commented that he "couldn’t be the same player that [he] was in Montreal in Toronto," as he could not play with "that same passion and heart for a team that, for eight years, was your most talked about rival".

[23] On October 14, 2017, the Maple Leafs beat the Canadiens 4–3 in overtime, ending a record-breaking 14-game losing streak against their rivals dating back over three years to January 18, 2014.

[37][38] The Canadiens ultimately won the best-of-seven matchup 4–3 with a 3–1 victory in game seven, and went all the way to the Stanley Cup Finals for the first time since their 1993 championship season.

[42] As a result, the Montreal Canadiens had developed rivalries with several hockey clubs, in which the teams were linked to larger class, linguistic, and religious divisions in the country.

[43] In addition to the cities and provinces the teams were based in, the Canadiens found themselves associated with French Canada and, to a lesser extent, with Roman Catholicism and les Patriotes.

[43] However, after the Quiet Revolution of the 1960s produced a more equitable society in Quebec and an improved economic situation for francophones, the Canadiens–Maple Leafs rivalry became less associated with these larger divisions.

The NHL added the Ottawa Senators via expansion in 1992, but the Nordiques and original Jets moved to the United States in the mid-1990s, becoming the Colorado Avalanche and Phoenix Coyotes, respectively.

The rivalry is also featured in the murals of Toronto's College subway station, in a work by Charles Pachter called Hockey Knights in Canada.