Canadiens vs. Maple Leafs – Rekindling the NHL’s Oldest Rivalry

It’s always a special night when the Montreal Canadiens and Toronto Maple Leafs suit up to hit the ice. Not only is it the oldest rivalry in the National Hockey League, some would argue it’s one of the most monumental matchups in all of professional sports.

The Past

The Canadiens and Maple Leafs have met in the playoffs 15 times in Stanley Cup history, with Montreal winning eight of these matchups. This rivalry reached its pinnacle in 1967, the year Canada celebrated its centennial year of Confederation. Montreal was hosting Expo ’67 and was ready to plan a parade down Saint Catherine Street until Toronto, the considerable underdog, spoiled the party and upset the Habs to capture their 13th and most recent Stanley Cup victory.

After the 1967 season, these matchups cooled down slightly due to the NHL expansion and Conference realignments. For most of the 80’s and 90’s, Toronto competed in the Western Conference and Montreal played in the East. New franchises in Vancouver, Calgary, Edmonton and Winnipeg also diluted allegiances, giving fans other Canadian teams to cheer for.

During these years, Montreal and Toronto only met a couple times during the regular season and if all stars aligned, would only meet in the playoffs if both teams went all the way to the Stanley Cup Finals. This dream looked like it may become a reality in 1993, when Montreal won the Wales/Eastern Conference Championships and Toronto was playing in the Campbell/Western Conference Finals. What a party this would have been to celebrate the 100th anniversary year of the Stanley Cup! However, it was not meant to be. The 1993 Los Angeles Kings, led by the ‘Great Gretzky’ narrowly defeated the Leafs to go on to play Montreal for the Stanley Cup. This would be the most recent Stanley Cup victory for the Habs.

Patrick Roy of the Montreal Canadiens
Canadian professional hockey player Patrick Roy of the Montreal Canadiens hoists the Stanley Cup over his head as he celebrates their championship victory over the Los Angeles Kings, Montreal, Canada, June 9, 1993. (Photo by Bruce Bennett Studios/Getty Images)

The Present

In 1998, the Leafs moved back to the Eastern Conference and yet another realignment in 2013, kept these two epic franchises in the same Division – the Atlantic Division (the old Atlantic Division was renamed the Metropolitan Division). This juggling of the Divisions has rekindled the past and the competition is as fierce as the days of the ‘Original Six’.

The NHL schedule now has Montreal and Toronto squaring off four times during regular season play. These games are usually tight matchups, with four of their last five meetings (one this season and four in 2018-19), being decided in overtime with Toronto claiming victory in three games out of the last five. The action is thrilling, the fans are wholehearted and the games are electrifying!   

Toronto Maple Leafs John Tavares Montreal Canadiens Jesperi Kotkaniemi
Toronto Maple Leafs John Tavares takes a face off against Montreal Canadiens Jesperi Kotkaniemi (THE CANADIAN PRESS/Nathan Denette)

The Future

It’s been 53 years since Toronto has hoisted Lord Stanley’s Cup and 17 years since Montreal has had a chance to inscribe names on this majestic piece of hardware. This year also marks 41 years since fans have seen a playoff series between these two teams. Heck, that’s an eternity to any fan, and a lifetime to the new generation. 

With 31 teams in the league now, the competition is tighter than ever and there is little room for error. What will it take to bring the Cup back to Canada and will either of these teams be able do it? One thing is for certain – what a party it would be to have a rekindling of this rivalry at the highest level of NHL hockey. Fans would be in for a treat, no matter what colour jersey they choose to wear!

About Saturday Night

The Matchup: Montreal and Toronto will be playing their second head-to-head matchup of the season on Saturday night. The Leafs coming to the Bell on the second night of back-to-back games without their Captain, John Tavares. Edge: Montreal

The Goalies: Carey Price will be starting in nets for Montreal while Leafs backup goalie, Michael Hutchinson will be looking for his first win of the season for Toronto. Edge: Montreal

Mixing and Matching: Max Domi and Jonathan Drouin combined for one assist in their first game as linemates against the San Jose Sharks on Thursday. Coach Claude Julien will be looking for more production from his top players if they are to remain together. The Leafs second and third lines have been shuffling around like cards on the blackjack table since Tavares got injured but have produced with goals in each game without their captain. Edge: Toronto

Special Teams: Both teams can put the puck in the net but struggle to keep it out of their own. Montreal and Toronto are dead even on the power play, both at 25% power play percentage. Montreal’s penalty kill has been their nemesis sitting at 67.6% with Toronto marginally better at 78.9%. Edge: Toronto

Fasten your seatbelts and get ready as one of the greatest rivalries in all of sports continues this weekend!