It's hockey time in Toronto once again, and just like in previous seasons, it seems that the Maple Leafs have started the campaign against perhaps the oldest opponent available, the Montreal Canadiens.
The Maple Leafs will face off against the Canadiens in Scotiabank Arena on September 29 in the season opening match of the 2026 to 2027 National Hockey League campaign. It will be the seventh straight year the two Original Six teams have faced each other in their first match of the campaign, and their 24th meeting in a shared season opener, which is more than anyone else in NHL history.
However, things may be a bit different this year. The Toronto Maple Leafs head into the campaign with one of the most impactful roster changes in recent memory, while the Montreal Canadiens enter with momentum coming off last year's Eastern Conference Finals appearance.
A Completely Different Team of Maple Leafs
If anyone had paid attention to Toronto last year, they would know why this needed to happen.
The Maple Leafs ended their season from 2025 to 2026 with a record of 32 wins, 36 losses and 14 overtime losses, placing them eighth in the Atlantic Division without making it into the Stanley Cup Playoffs.
The reaction was swift.
Toronto brought about huge changes in its front office, coaching, goaltending, defense, and forwards. John Chayka became the team's general manager, with Jim Hiller taking the reins as its head coach. Onto the ice, the team acquired Sergei Bobrovsky, Darren Raddysh, Nick Paul, Jack Roslovic, Emil Andrae, Teddy Blueger, Colton Sissons and Brandon Duhaime. This is no small tweak at the margins.
Everyone’s Eyes Are Fixed on Gavin McKenna
The most intriguing new member of the Maple Leafs is also the youngest one. Toronto picked up Gavin McKenna first overall in the 2026 NHL Draft, getting themselves a very interesting young prospect.
Last year, McKenna had 51 points in just 31 games with Penn State, and Toronto has announced that he’ll get his chance to fight for a place among the top forwards of the team. It seems that McKenna will enter the NHL by facing one of the oldest hockey rivals – Montreal. Of course, expectations shouldn’t be too high since he is just 18 years old and a rookie of the NHL. However, Leafs fans will definitely want to see how quickly the kid gets used to playing with Toronto’s established forwards.
The Leafs have Auston Matthews, William Nylander, John Tavares, Matthew Knies, and now McKenna – lots of skill to play with.
The only question is how quickly these combinations will form into a real team.
Sergei Bobrovsky Adds to the Net Discussion
Yet another big storyline is Sergei Bobrovsky. Toronto inked the experienced netminder to a three-year contract in July and instantly made him their presumed starter between the pipes.
Bobrovsky brings plenty of playoff experience along with two Stanley Cups to his resume. But at age 37, the question for Toronto is whether Bobrovsky can still play well enough to help stabilize an organization coming off a disappointing year.
Toronto does not necessarily expect Bobrovsky to steal games for them. What the Leafs need is solid goaltending that allows a new-look roster some time to gel.
How Bobrovsky performs out of the gate thus becomes one of the key things to watch in the early part of Toronto’s season.
Opening with Montreal Is Not an Easy Challenge
This year, Montreal comes into the season from a vastly different spot.
Last season, the Canadiens ended up with a 48-24-10 record, finishing third in the Atlantic Division, while making it to the Eastern Conference Final.
For Toronto, it means that the game will be a valuable early season challenge.
Montreal has established a core of young players and goes into the season with legitimate expectations following their strong performance during the playoffs last season.
Instead of facing a team trying to find its feet, Toronto will be able to assess right away how well its new roster measures up against a divisional opponent who has made big strides during the previous season.
For Leafs' fans, it should make for an intriguing match-up.Certainly, Toronto doesn't have to figure everything out after just one game. However, how well they cope with Montreal's style of play and confidence can offer an early insight into whether the changes in the off-season have been the right ones.
What Should Leafs Fans Watch For This Season?
The easy question here would be whether Toronto returns to the postseason. But there are a number of smaller questions that will determine whether that occurs.
- Will McKenna be able to make an impact right away?
- Will Bobrovsky give some stability to the goaltender position?
- Will Darren Raddysh provide depth to a Toronto defense that the organization wanted to improve?
- Will Toronto create more sustained pressure offensively after having trouble maintaining possession of the puck last season?
- And perhaps most importantly, how quickly will a team with this many new faces find some chemistry?
Toronto does still have its core players.Matthews remains their center point. Nylander is still one of their top offensive weapons. Tavares brings his veteran experience, and Knies is still an important piece of their forwards.
The difficulty is creating something consistent surrounding them. One Opening Night will not be able to answer all of these questions. Even the first month will likely fall short on providing enough answers.
But when a team makes this many moves in one offseason, it is safe to say that the start of the season will certainly be much more intriguing.
Toronto and Montreal Are Set for Many More Meetings
The feud isn’t done after opening night. The NHL’s expansion of the season from 82 games to 84 games for 2026 to 2027 means each team plays every divisional foe four times in the regular season. In other words, Toronto and Montreal get several opportunities to see how they measure up against one another throughout the year.
As for Toronto, those games against Atlantic Division opponents might prove crucial if the Leafs are struggling to get back into the playoffs. It also means that there’ll be many more nights in downtown Toronto when blue and white fly, and so do some Montreal jerseys.
Going to a Leaf Game in Downtown?
Are you driving into downtown Toronto for your upcoming game this season? Well, you can make it a productive one as well!
The financial district location of ALPHASHINE where you can get your car detailed is situated at 181 Wellington Street West near Scotiabank Arena in the parking garage of Ritz Carlton Hotel.
Free parking will be included in your ALPHASHINE appointment, which could be quite helpful considering that you are going downtown anyway. Get your car cleaned in advance, leave your car at ALPHASHINE, go straight to the arena.
You can learn about all ALPHASHINE locations in Toronto or book your next appointment through our website.
