Toronto Maple Leafs v Montreal Canadiens: All you need to know about Canada's oldest NHL rivalry

Commonly referred to as the fiercest rivalry in hockey, the bad blood between the Toronto Maple Leafs and Montreal Canadiens can be traced back to the creation of the NHL in 1917 when both franchises entered the league as part of the Original Six.

For the first 25 seasons, the rivalry was a relatively tranquil one with the teams focusing on establishing themselves, and only coming together twice in the Stanley Cup Playoffs.

Sole focus after Maroons folded

In 1938 though, everything changed as the Montreal Maroons were forced to fold from the NHL, leaving the Canadiens and the Leafs as the only two teams based in Canada.

That natural rivalry was heightened between 1944 and 1967 as the teams competed against each other 11 times in the post-season with the Stanley Cup mainly being won by one or the other.

Montreal held the upper hand between 1956-1960 winning an NHL record five champions in a row before a role-reversal saw the Leafs win three Cups in a row.

Cup competition drives rivalry

The two continued to go toe-to-toe for several years afterwards, in the end sharing a combined 12 of 13 Stanley Cups between 1956 and 1969.

Since, the Canadiens have won ten more Stanley Cups, but the wait continues to go on for the Leafs who have not won a Cup or even reached the Stanley Cup Final since 1967. It is the longest drought of any NHL team and a record continually mocked by Canadien fans.

Off the ice, societal issues during the mid-20th century heightened the original rivalry with the two teams becoming a representation for a variety of cultural dualities in Canadian society; most notably with the Canadiens representing French-speaking Canada and Roman Catholicism, and the Maple Leafs the English-speaking part of the country and Protestantism.

Montreal hold bragging rights

In history, the Canadiens and Maple Leafs have met in 16 Stanley Cup playoff series, including five Stanley Cup Finals. 

Montreal hold the bragging rights with a 9-7 series advantage, winning 46 games compared to the Leafs' 32.

Their most recent meeting came during the 2021 playoffs - their first postseason meeting for 42 years - where the Leafs let slip a 3-1 series lead to lose in a Game 7.

If that wasn't bad enough, Montreal went all the way to the Stanley Cup Final where they were defeated by the Tampa Bay Lightning. 

Meanwhile, the Leafs were left to continually feel inferior, but finally ended their playoff series drought at least in 2022/23 by beating the Tampa Bay Lightning in the first round. They were of course dumped out by the Florida Panthers in the next.

The battle for supremacy has continually shifted over the years, not just in the playoffs but in the regular season too.

Regular Season head to head

Montreal Canadiens wins	366
Toronto Maple Leafs wins	299
Ties	88

Playoff head to head

Montreal Canadiens wins	46
Toronto Maple Leafs wins	32

Tide turning

From 2014-17 the Canadiens achieved an incredible 14-game winning streak over their arch rivals but more recently with the likes of Auston Matthews and Mitch Marner rejuvenating Toronto's franchise, the Leafs enjoyed a seven-game winning run from 2017 to 2019. 

Bringing the argument up to the current date, the Leafs and Canadiens each won two games against each other in the 2022/23 NHL regular season.

Leafs in the ascendancy

After leading the league in goals scored for two straight seasons, Leafs star Auston Matthews' production dropped as he scored 40 goals in 2022/23.

His Leafs teammate William Nylander also chipped in 40 goals last season, but the Leafs made Matthews the highest-paid player in the league this summer, so they'll want him to return to his best to break the team's long Cup drought.

In all, four players - Marner, Nylander, Matthews, and captain John Tavares - scored over 80 points in the 2022/23 season.

But overall, despite a second-round playoff defeat to eventual Stanley Cup finalists, the Panthers, optimism and confidence remain high in a Toronto franchise led by head coach Sheldon Keefe. 

Behind the scenes though, former Calgary Flames general manager Brad Treliving has taken the reins from Kyle Dubas, who had been with the franchise since 2014 but is now in Pittsburgh after his contract was not renewed.

Rebuild is on in Montreal

The Canadiens on the other hand are in the state of flux with former General Manager Marc Bergevin being fired in the middle of 2021/22 following a decade in charge, to be replaced by Kent Hughes. 

Coach Dominique Ducharme was also replaced in that season by Martin St. Louis, a Hall of Fame player, but with little experience behind an NHL bench, and that showed in the final standings.

The Cup final appearance of 2021 was quickly consigned to the memory banks as the Canadiens finished last in the league for the first time since 1939-40 the following season, setting franchise records for most regulation losses (49), fewest wins (22), fewest points (55) and more goals against (319), in 2021/22.

Montreal did marginally improve last season, finishing fifth-last with a 31-45-6 record, but the rebuild remains very much on going into 2023/24.

Led by a pair of quality young centres in captain Nick Suzuki and Kirby Dach, the Canadiens have a decent young core to build around but it looks likely that it will take some time before they are challenging for honours on a consistent basis once again.

2023/24 Odds

The disparity between the two rivals' current standing in the NHL is reflected in the odds with the Maple Leafs listed as the +800 favorites to win Stanley Cup 2023/24, while the Canadiens are on offer at a huge +12500 with only two teams at bigger odds - the San Jose Sharks and the Anaheim Ducks. 

Toronto also lead the betting at +200 to win the Atlantic Division with Montreal the outsiders at +7500, while the Habs are priced at +1025 to even make the playoffs. 

Only one team is shorter than the Leafs at +650 to win the Presidents' Trophy - the Carolina Hurricanes at +600 - and in a relevant contrast, only two sides are shorter than the Canadiens at +550 to finish last in the league standings.