The history of the hockey rivalry between Montréal and Toronto is nearly as old as professional hockey itself, dating back to the early days of the game’s inception, and all the way through the evolution of the game as we know it today. Some of the biggest names in hockey have laced up for either the Leafs or Canadiens (and sometimes both), with many of the battles between these squads entering into the annals of hockey history, with the biggest dates in the rivalry’s century-plus story showcased here.

Dec. 4, 1909 – The Montréal Canadiens are founded as a charter member of the National Hockey Association, intended to represent Montréal’s francophone community (despite being owned by anglophone Ambrose O’Brien) as an alternative to the Montréal Wanderers, who joined the NHA with a large anglophone following. Toronto is granted a franchise, the Blueshirts, two years later.

Nov. 26, 1917 – Out of a desire to leave the NHA over disputes with Toronto Blueshirts owner Eddie Livingstone, the Canadiens, Montréal Wanderers, Ottawa Senators and Québec Bulldogs form the National Hockey League following several meetings at Montréal’s Le Windsor Hotel. However, as the owners were aware of Québec’s major financial troubles, and looking to have a team based in Toronto, a temporary franchise is awarded to the Toronto Arena Company in place of the now defunct Bulldogs, colloquially known as the “Arenas,” to round out the new NHL.

Dec. 26, 1917 One month after the creation of the NHL and the Toronto team, the Arenas and the Montréal Canadiens face off for the first time ever at the Arena Gardens in Toronto, with the Arenas winning 7-5, the opening chapter of a century-old rivalry. Arenas defender Harry Cameron led the way with four goals and an assist, also getting into a fight with Canadiens captain Newsy Lalonde, with both notching the first ever “Gordie Howe Hat Trick,” thirty years before Gordie Howe’s pro career began (and over a decade before his birth).

Dec. 29, 1917 In their second meeting just three days later at Arena de Montréal, the Canadiens defeat the Arenas 9-2 for their first victory in the rivalry’s history, as well as the first game of the rivalry to be played in Montréal. However, this was the only game ever played between these two here, as the arena burned down just four days later, forcing the Habs to move back to the Aréna Jubilée, where they had originally played until 1910 in the NHA.

Jan. 28, 1918When a brawl between “Bad” Joe Hall and Alf “Dutch” Skinner becomes so overheated they begin swinging sticks at each other, with Skinner being knocked unconscious and having to be carried off the ice, both men are arrested by Toronto police for disorderly conduct in the locker rooms at Arena Gardens. Both were granted bail and faced a judge in a Toronto court the following day, being fined $15 apiece.

Mar. 13, 1918 In their first playoff meeting to determine the NHL champion to play for the Stanley Cup, the Canadiens defeat Toronto 4-3 at Aréna Jubilée. Despite the win, the Arenas’ 7-3 victory two days earlier advances them to the Stanley Cup, winning 10-7 on aggregate goals. Toronto would go on to defeat the Pacific Coast Hockey Association’s Seattle Metropolitans in five games to win their first Stanley Cup.

Feb. 15, 1919 – The Canadiens beat the Arenas 8-2 in what would be the rivalry’s final game at Aréna Jubilée, as the rink burned down on April 23, the second Canadiens arena to burn down in two years.

Dec. 22, 1919 – With the Arenas for sale due to a lawsuit from Livingstone over the right to use Arena Gardens, team manager Charlie Querrie leads a group of investors to buy the team and rename them the Toronto St. Pats, the name owing to the OHA amateur team many of the investors managed the previous year.

Jan. 10, 1920 Montréal thrashes the St. Pats. in a 14-7 victory, on the back of a six goal and seven point performance from Newsy Lalonde, setting an NHL record for the most combined goals in a game of 21, which has yet to be eclipsed, and only tied in one other instance ever, a 12-9 Edmonton victory over Chicago in 1985.

Nov. 29, 1924 Forced to vacate Aréna Mont-Royal due to an ice-making problem, the Canadiens unexpectedly host Toronto to open their season at the just-completed Forum de Montréal, defeating the St. Pats 7-1. This marked the first of 321 such meetings in 72 years of hockey at the Forum, which was originally constructed to only host the Montréal Maroons, as the Canadiens would make the Forum their permanent home two years later.

Mar. 13, 1925 In their second and final meeting for the O’Brien Trophy (and NHL Championship), the Canadiens sweep the St. Pats in two games to win their series by a 5-2 aggregate score, moving on to face the Western Canada Hockey League’s Victoria Cougars for the 1925 Stanley Cup, which they would lose three games to one.

Feb. 14, 1927 – After turning down a more lucrative offer to move the team to Philadelphia, the St. Pats are sold by Querrie to the coach of the University of Toronto Varsity Blues, Conn Smythe. Upon taking control, Smythe renames the squad the Maple Leafs, in honour of his World War I regiment. The Leafs played the rest of the 1926-27 season in the St. Pats’ green and white, but the following season would reintroduce the now-familiar blue and white sweater.

Nov. 14, 1931 The Canadiens and Maple Leafs meet for the first time at Maple Leaf Gardens, playing to a 1-1 draw, marking the first of 327 total meetings here over a nearly seventy year period.

Oct. 1, 1933 – In a highly polarizing move in both cities, the Canadiens trade star goaltender (and native Torontonian) George Hainsworth to Toronto for fellow top goalie (and native Montréaler) Lorne Chabot, in an attempt to boost attendance and local fanfare by adding locals to the roster. Chabot proves to be a bust, spending just one season in Montréal before being traded to Chicago, while Hainsworth spent three seasons in Toronto before retiring.

Nov. 10, 1934 – After adding the penalty shot to the NHL rulebook to start the 1934-35 season (albeit in a very different format from today, featuring the player shooting from a stationary circle 38 feet from the goaltender), first penalty shot in NHL history is awarded after Maple Leaf Bill Thoms hauled down Canadien Georges Mantha on a breakaway. Teammate Armand Mondou was selected to shoot for Montréal against George Hainsworth, who easily stopped the shot.

Mar. 16, 1935 After defender Red Horner and goalie George Hainsworth are both lost to injury during a game, “The Big Bomber” Charlie Conacher plays forward, defence and goaltender in a single game, stopping four shots in his short stint in goal, not to mention netting three goals of his own into the Canadiens’ net on the evening, setting the NHL record at the time for most goals in a season with 35.

Dec. 28, 1939 After a second Canadiens goal is called back by referee and former Maple Leaf King Clancy, a raucous Forum crowd showers the ice with programs, garbage and even fruit. When summoned to the Canadiens bench by team president Ernest Savard, Clancy and linesman (also former Leaf) Hap Day are both physically attacked by Savard, who has to be separated by Habs coach Pit Lepine. The game descends into chaos, first with a fan attempts to stop a Gordie Drillon breakaway by tossing a fedora on the ice, and a later Habs goal incensing Leafs goalie Turk Broda so much that he too accosts Clancy. Clancy’s miserable evening ends with a high stick in the face from Canadien Johnny Gagnon, who he declined to penalize over the accident.

Feb. 17, 1940 With World War II now six months underway, this Saturday night meeting becomes the first recording of the Imperial Oil Hockey Broadcast (a forerunner to the current Hockey Night In Canada) to be edited for Canadian troops in Europe. The 3-1 Toronto victory was edited down to a 30 minute record that was then transmitted first to Lawrenceville, Québec, and then via shortwave radio across the Atlantic Ocean to the United Kingdom, where the British Broadcasting Corporation broadcast the highlights to Canadians stationed overseas.

Apr. 17, 1940 – At the recommendation of Smythe to Canadiens GM Tommy Gorman, the Habs sign former Leafs coach Dick Irvin as their head coach following a dismal season. Smythe announces former captain Hap Day as the new coach of the Leafs the following day. Irvin would spend the next fifteen years behind the Montréal bench, making the Stanley Cup finals eight times and winning championships in 1944, 1946 and 1953, while Day would serve as Leafs coach for ten seasons, winning five Stanley Cups (1942, 1945, 1947-49).

Feb. 20, 1941 – The Maple Leafs extend their unbeaten streak against Montréal to fourteen games (dating back to December 1939) with a 2-1 home victory, marking the longest undefeated streak by Toronto in the history of the rivalry.

Sep. 10, 1943 – Toronto trades star defenceman Frank Eddolls for the rights to sign 17 year old forward Ted Kennedy, a trade orchestrated by Leafs interim GM Frank Selke, filling in for Conn Smythe away on duty in World War II. Smythe returned incensed to find that Eddolls was traded without his consultation, driving a wedge between him and Selke that resulted in Selke leaving Toronto in May 1946. While the trade ended up being a boon for Toronto on the ice, with Kennedy leading the Leafs to five Stanley Cups, Selke’s subsequent jump to Montréal the next season proved perhaps more beneficial, as he not only managed the Canadiens for six Stanley Cups, but developed their extensive farm team system that led to Montréal’s unrivalled success well beyond his departure in 1964.

Mar. 23, 1944 In Game Two of the Stanley Cup Semifinals, Maurice “Rocket” Richard explodes for an NHL record five goals against the Leafs in just a 30 minute span, carrying the Habs to a 5-1 victory to tie the series at 1-1. Richard, in only his second career playoff game, was named the game’s first, second and third star, and both Toronto and Montréal papers the following day declared the victory as “Richard 5, Toronto 1.”

Feb. 25, 1945 – With previous record holder “Phantom” Joe Malone in attendance at the Forum, Maurice Richard notches his 45th goal of the season, breaking the 27-year old record. Malone presents Richard with the historic puck, and three weeks later Richard would become the first player in history to score 50 goals in a season, achieving the astonishing mark in 50 games.

Apr. 8, 1947 For the first time in their thirty year rivalry, and after fifteen previous playoff games, the Canadiens and Maple Leafs finally meet to crown a Stanley Cup champion. The Maple Leafs win the Cup eleven days later, winning the series in six games on home ice.

Jan. 19, 1950 – Despite a 4-2 loss to the Leafs, Dick Irvin coaches the Canadiens in his 1,000th game, becoming the first head coach in NHL history to reach the milestone. He would coach a total of 1,449 games in his career, which ended in 1955-56 with Chicago.

Apr. 21, 1951 The Leafs win the Stanley Cup in five games during their second Finals meeting against the Canadiens. This series also set a record as all five games went to overtime, with four of the five games ending in a 3-2 score. What would end up being Bill Barilko’s final goal before his untimely death that summer famously won the Leafs the Cup.

Oct. 29, 1952 Despite losing a 7-5 contest to the Leafs, Rocket Richard ties Nels “Old Poison” Stewart as the all-time NHL leading goal scorer, after netting two first period goals to bring his career total to 324.

Dec. 9, 1953 A late melee at Maple Leaf Gardens results in a record 204 penalty minutes and fifteen misconducts, leaving each team to finish the game with only three skaters each for the final 108 seconds.

Dec. 29, 1954 After another rivalry game at Maple Leaf Gardens ends in a fracas, with third period fights between Bert Olmstead and Tim Horton, followed by Maurice Richard tilting with both Leaf forward Bob Bailey and linesman George Hayes in a nearly ten minute brawl, Leafs owner Conn Smythe famously quips on the controversial topic of violence in hockey: “We’ve got to stamp out this sort of thing, or people are going to keep on buying tickets.”

Mar. 10, 1955 A year after debuting at the Boston Garden, this 0-0 tie game in Montréal marks the first time a Zamboni ice resurfacing machine is used in Canada for ice hockey, ending nearly four decades of tedious shovelling and hand flooding ice between periods.

Dec. 28, 1955After nearly 40 years of wearing cream or orange sweaters, this game at the Montréal Forum marks the debut NHL on-ice officials wearing the now-familiar black and white striped “zebra” uniforms.

Dec. 29, 1955 Although he would notch his 500th regular season goal two years later, “Rocket” Richard still sets history tonight by netting his 500th total career goal, counting both regular season and playoffs, to open the scoring on Harry Lumley in a 5-2 Habs win. 

Mar. 12, 1958 – Maurice Richard scores twice in a 5-3 victory over the Leafs, bringing his all-time total goals scored in the rivalry to an even 100. Richard would score eight more goals against the Leafs before his retirement, setting a record for rivalry goals that has not come close to being broken in the 60+ years since; the closest to eclipsing him was fellow Hab Jean Béliveau, who finished his career with 74.

Apr. 18, 1959 In their third Stanley Cup Finals meeting, the Canadiens win their fourth straight Stanley Cup, and first over Toronto, winning in five games.

Apr. 14, 1960 The Canadiens and Leafs meet one year later for hockey’s ultimate prize, this time with the Canadiens repeating as champs (winning their record fifth consecutive Cup), sweeping the Leafs 4-0 in the series, and shutting out the Leafs in the deciding Game Four by the same score. The game would serve as Maurice Richard’s final before his retirement, and he thanked the Toronto crowd in English following the game: “It’s always nice to win the Cup outside of Montréal. But the best place to win it is right here in Toronto.”

Oct. 30, 1963 – A brawl on the penalty bench between Leaf Bob Pulford and Canadien Terry Harper (with NHL President Clarence Campbell in the crowd, no less) prompts the National Hockey League to institute separate penalty boxes for each team, rather than a single bench for all players.

Apr. 9, 1964 – The Maple Leafs edge the Canadiens by a score of 3-1 on the strength of a Dave Keon hat trick to win Game Seven of their Semifinal and advance to the Stanley Cup Finals, the first playoff series between these teams to go a full seven games.

Mar. 24, 1965 Thirteen years after the first hockey game was broadcast on television, hockey’s first game is broadcast in colour, with hockey fans across Canada seeing the blue and white Maple Leafs defeat the bleu, blanc et rouge Canadiens 3-2 on a Wednesday night at Maple Leaf Gardens. The game also featured the first camera to be placed behind a net, the first such incarnation of the modern goal camera, which captured a failed Yvan Cournoyer penalty shot in the third period on Johnny Bower.

Feb. 9, 1966 – The NHL announces expansion of the league from the “Original Six” to twelve new teams for the 1967-68 season, with six teams forming the new West Division: the Oakland Seals, Los Angeles Kings, Minnesota North Stars, Philadelphia Flyers, Pittsburgh Penguins and St. Louis Blues. The original franchises, including Toronto and Montréal, stay as division rivals in the East Division, made up of the Original Six squads.

Nov. 19, 1966 In the 500th meeting between these teams, the Maple Leafs win their second straight over Montréal with a 5-1 victory, with Ron Ellis notching two goals and an assist.

May 2, 1967 In their fifth (and so far latest) meeting over the Stanley Cup, the underdog Maple Leafs win the Stanley Cup in six games over the Canadiens, in the centennial year of Canadian confederation, and in the middle of Montréal hosting the 1967 World Expo. This victory marks not only the last Stanley Cup meeting between these rivals, but the last finals appearance championship for the Maple Leafs.

Oct. 1, 1974 – Thanks to the NHL adding the Kansas City Scouts and Washington Capitals, the league announces expansion from two Divisions to four, within two new conferences, for the following season. The Leafs are shifted to the Adams Division and the Canadiens the Norris Division, both part of the Prince Of Wales Conference.

Mar. 1, 1979 – In one of the strangest staffing moves in NHL history, Leafs owner Harold Ballard declared to the media that if the Maple Leafs fell to the Canadiens in a crucial matchup in Montréal, coach Roger Neilson would be fired. However, with the Maple Leafs trailing 2-1 in the third period, Ballard announced Neilson was being relieved of his duty during the game itself. Two nights later, Neilson returned behind the bench in Toronto against Philadelphia, only after a failed attempt by Ballard to have Neilson emerge on the bench with a paper bag over his head; Ballard claimed Neilson was only “on furlough for a day or two.”

Apr. 22, 1979 The Canadiens eliminate the Maple Leafs from the Stanley Cup Playoffs by sweeping their Quarterfinal series, winning in overtime on a Larry Robinson power play tally after a controversial high stick from Dave “Tiger” Williams, resulting in Williams attempting to attack referee Bob Myers after Robinson’s series winner.

Dec. 10, 1981 – The NHL announces that due to rising travel costs for many teams, the Norris Division would move to the Campbell Conference the following season (in place of the departing Patrick Division), putting the Leafs in separate conference from the Canadiens for first time in league history. As part of the realignment, the Canadiens would also move from the Norris to Adams Division in the Prince Of Wales Conference.

May 29, 1992 – Canadiens head coach (and Québec native) Pat Burns resigns from the organization – only to be hired later that same day to coach the rival Maple Leafs.

Mar. 31, 1993 – The NHL announces the end of the current divisional system for the 1993-94 season, with teams now to be organized by geography, in the newly-formed Eastern and Western Conferences. The Canadiens are to play in the Northeast Division in the East, and the Maple Leafs in the Central Division in the West.

May 29, 1993 – The Maple Leafs come within one game of facing the Canadiens in the 1993 Stanley Cup Finals, which would have been their first Finals meeting in nearly 30 years, meeting for the centennial anniversary of the Stanley Cup. However, due to a controversial finish in Game Six of their Campbell Conference Final against the Los Angeles Kings, the Leafs fall in Game Seven by a 5-4 score, backed by a Wayne Gretzky hat-trick. The Canadiens would go on to win their 24th Stanley Cup over the Kings in five games.

Oct. 21, 1995 The Leafs and Habs face off for the final time at the Forum de Montréal, with the Canadiens edging out the Leafs in a 4-3 victory on a last-second Pierre Turgeon goal, just nine days away from the 1995 Québec independence referendum, where Québec voted to remain part of Canada with a narrow 50.58% victory. The game marked the first for controversial new Habs general manager Réjean Houle and head coach Mario Tremblay, who, despite no previous managerial experience, were appointed by team president Ronald Corey that morning to replace Serge Savard and Jacques Demers, respectively, who six weeks later would engineer the controversial trade of star goalie Patrick Roy.

Feb. 22, 1997 Well over a year after moving in to the new Centre Molson, the Leafs finally meet the Canadiens in their new rink, upsetting the home fans with a dominant 5-1 victory.

Dec. 7, 1997 – After years of petitioning the league to change conferences, spurred by Maple Leafs team president, Toronto native and former Canadiens Hall of Famer Ken Dryden, the NHL approves a plan to move the Leafs from the Western to Eastern Conference for the 1998-99 season (as part of a larger league realignment), bringing them back into the same division (this time the Northeast) with the Canadiens, after a nearly twenty year separation.

Jan. 7, 1998 – After eighty years of Montréal and Toronto being the most frequent opponents in NHL history, the Canadiens defeat the Boston Bruins 2-1 in overtime in their 636th meeting, outpacing the Leafs-Canadiens rivalry for the first time due to their conference separation in 1981, despite Boston not joining the NHL until 1924, eight seasons after the league was founded.

Dec. 26, 1998 The Canadiens play their final game at Maple Leaf Gardens, defeating the Leafs 2-1 in a Boxing Day victory, with a late Stéphane Quintal goal standing as the game-winner.

Feb. 20, 1999The Maple Leafs open their new home, the Air Canada Centre, with a narrow 3-2 overtime victory over the Canadiens, with Steve Thomas scoring the winning tally over Jeff Hackett in the first event hosted at the arena.

Oct. 7, 2006 – For the first time in their rivalry, the Maple Leafs and Canadiens settle a game with a penalty shootout, a new rule instituted by the NHL the previous season. The Habs notch a 3-2 victory in Toronto, with Michael Ryder scoring the winning penalty shot on Toronto goalie Andrew Raycroft.

Jan. 8, 2009 – The Canadiens host the Maple Leafs to help kick off their centennial celebration, honouring the rivalry with a ceremonial faceoff between the Canadiens, represented by Jean Béliveau, Phil Goyette, Guy Lapointe, Peter Mahovlich, Steve Shutt and Vincent Damphousse, and the Maple Leafs, represented by Johnny Bower, Darryl Sittler, Wendel Clark and Félix Potvin.

Mar. 14, 2013 – The NHL unveils a new conference lineup for the following season, with the intention of keeping teams in their respective time zones. The Eastern Conference, now with sixteen teams to the West’s fourteen (sixteen as of 2021), still keeps the Canadiens and Maple Leafs, both members of the newly named Atlantic Division.

Jan. 7, 2017 – Montréal wins their thirteenth straight contest against the Maple Leafs (with a streak dating back to March 2014) in a 5-3 victory at the Air Canada Centre, marking the Canadiens’ longest unbeaten streak against Toronto in the history of the rivalry, and the longest consecutive win streak for either team. The streak is extended with a fourteenth win on February 25, tying the longest undefeated streak in the rivalry’s history with Toronto’s 14-game streak from 1939 to 1941 and marking the rivalry’s longest win streak ever.

Jan. 27, 2017 – 46 former Maple Leafs and Canadiens stars are named to “The NHL Top 100” at a ceremony in Los Angeles, honouring the top players from the first century of NHL hockey, with 22 players being named from Toronto, 21 from Montréal, and three players (Frank Mahovlich, Dickie Moore and Jacques Plante) named that played for both teams.

Nov. 18, 2017 – To celebrate the centennial of the NHL’s founding in Montréal, the league holds a General Managers meeting in Le Windsor Hotel just shy of the 100 year anniversary, and the Canadiens host the Maple Leafs at Centre Bell, with the ceremonial puck drop conducted by Hall of Fame representatives of each Original Six team, with Yvan Cournoyer representing the Canadiens and Dave Keon representing the Maple Leafs.

Dec. 20, 2020 – After the 2019-20 season had to be finished in “bubbles” in Toronto and Edmonton due to the global COVID-19 pandemic, and due to COVID-related delays between the league, players association and local governments, the NHL announces a 56-game shortened 2020-21 season, with all seven Canadian teams (Montréal and Toronto, along with the Ottawa Senators, Winnipeg Jets, Calgary Flames, Edmonton Oilers and Vancouver Canucks) realigning to a “North Division” for the season due to travel restrictions between Canada and the United States; teams only play within the division, meaning that the ten meetings between the Canadiens and Leafs marks the most in a season since 1967-68.

Feb. 20, 2021 The Maple Leafs and Canadiens meet in the regular season for the 751st time, surpassing Montréal and Boston for the most frequent matchup in NHL history once again for the first time in nearly a quarter century. This is due both to the COVID-19 restricted North Division for the 2020-21 season, as well as travel restrictions eliminating regular season play between the Canadiens and Bruins; pending another divisional realignment, Montréal and Toronto should now hold this top spot for decades to come.

May 31, 2021 Meeting in the playoffs for the first time in 42 years in the Stanley Cup Quarterfinals, the Canadiens shock the Maple Leafs, up 3-1 in the series, by winning Games Five and Six in overtime (following multiple-goal leads blown in both games), and roaring back to win the series in Toronto on the backs of a 3-1 victory in Game Seven, just the second series (and first in nearly sixty years) between these two to go the distance.