The 2026-27 season is 71 days away and last week, the National Hockey League announced their first 84-game schedule in over 30 years. The two additional games added to the league's schedule will be used for divisional matchups and should create some interesting storylines as the season rolls along.
After reaching the Eastern Conference Final last season, the Montreal Canadiens are hoping that they can replicate the success they had last season and even push for an Atlantic Division title. With almost every team in the Atlantic improving in the offseason, it's going to be an intense fight from Game 1 in September all the way to Game 84 in April.
Let's take a look at ten must-watch games on the Canadiens' schedule for the upcoming 2026-27 season.
Ten must-watch Montreal Canadiens games during the 2026-27 season
2026-27 regular season opener - Tuesday, September 29th vs Toronto Maple Leafs
Starting us off is the first game of the 2026-27 season, which is set for Tuesday, September 29th against the Toronto Maple Leafs. With the increase in the amount of regular season games, we're seeing a September start for the first time since 2007, when the league staged a pair of games in London, England.
As is the case mostly every season, the Canadiens will begin the new campaign against the Toronto Maple Leafs, who are coming off a tough year. The Maple Leafs landed themselves the first overall pick in the 2026 NHL Entry Draft after winning the Draft Lottery and selected Gavin McKenna.
Montreal won the season series against the Maple Leafs in 2025-26 with three wins and only one loss, which came on opening night last October.
2026-27 home opener/2026 Eastern Conference Final rematch - Tuesday, October 6th vs Carolina Hurricanes
After starting the season with a pair of games on the road, the Montreal Canadiens will play their first home contest of the 2026-27 campaign on October 6th against a team they know quite well from this past spring - the Carolina Hurricanes.
Montreal's home opener will be the first of three meetings between them and the Hurricanes this season. It'll be a rematch of last season's Eastern Conference Final, which the Hurricanes downed Montreal in five games and would eventually go on to win their second Stanley Cup in franchise history over the Vegas Golden Knights.
In front of a raucous Bell Centre crowd for the home opener, it'll be a perfect opportunity for Martin St. Louis' group to avenge last season's loss in the Conference Final.
Second round rematch/NHL Frozen Frenzy - Tuesday, October 13th vs Buffalo Sabres
The National Hockey League's Frozen Frenzy will returns for the fourth season. For those who aren't familiar, the Frozen Frenzy is held on a weeknight in October with all 32 teams in action at staggering start times.
This year, the Montreal Canadiens will be taking on the Buffalo Sabres in a rematch of last season's second round series. The Canadiens came out on top in that series, with Alex Newhook scoring the overtime winner in Game 7 to send Montreal to their first Eastern Conference Final since 2014 (2021 Montreal was technically part of the Western Conference for the third round).
The Buffalo Sabres have made some moves this summer Alex Tuch and Bowen Byram departing for the Washington Capitals and Chicago Blackhawks, respectively. Buffalo's most notable addition in the offseason thus far came in late June when they acquired defenseman Olen Zellweger from the Anaheim Ducks.
2026 Heritage Classic - Sunday, October 25th vs Winnipeg Jets
For the first time in nine years, the Montreal Canadiens return outdoors. In late October, the Canadiens will head to Princess Auto Stadium in Winnipeg to take on the Jets in the 2026 Heritage Classic.
This marks Montreal's first outdoor game since the NHL 100 Classic in 2017 and their fifth outdoor game in franchise history - 2003 Heritage Classic, 2011 Heritage Classic, 2016 Winter Classic, 2017 NHL 100 Classic. Montreal has a 2-2-0 record in outdoor games, with wins coming in 2003 and 2016 against the Edmonton Oilers and Boston Bruins, respectively.
Given how early on in the season the Heritage Classic is, it wouldn't shock me if we see an announcement on the uniform the Canadiens will wear at some point in early September, before training camp gets underway.
First round rematch - Wednesday, December 2nd vs Tampa Bay Lightning
The first game of December for the Montreal Canadiens will see them take on the Tampa Bay Lightning at the Bell Centre on Wednesday Night Hockey.
It'll be the first meeting between the two teams since they faced each other in the first round of the Stanley Cup Playoffs in the spring. Montreal came out on top in that series in seven games thanks to some stellar goaltending from Jakub Dobeš. Montreal won game seven on the road in Tampa Bay by a score of 2-1, despite only firing nine shots on Lightning netminder Andrei Vasilevskiy.
The Lightning lost a big piece of their defensive corps this summer as they dealt pending unrestricted free agent Darren Raddysh to the Toronto Maple Leafs, who then inked him to an eight-year contract. While replacing Raddysh's production won't be an easy task, the Lightning are hoping that former Stanley Cup champion John Carlson, who they signed earlier this month, will be able to help contribute offensively.
First game vs Ottawa - Sunday, December 6th vs Ottawa Senators
The Montreal-Ottawa rivalry will be reignited in early December as the Canadiens host the Senators on the second half of a back-to-back. It'll be the first game between the two teams in the post-Brady Tkachuk era after he was traded to the Florida Panthers, where he'll play with his brother Matthew, back in June.
As was the case against the Toronto Maple Leafs, the Montreal Canadiens won the season series over the Ottawa Senators with three victories and one loss. Samuel Montembeault, who has an uncertain role heading into the 2026-27 season, picked up two of the three wins against Ottawa, while Jacob Fowler recorded the other.
The Ottawa Senators are hoping to make it back to the Stanley Cup Playoffs for a third consecutive season, but will have to do so without their now-former captain. Adding Andre Burakovsky in a trade with the Chicago Blackhawks was a nice depth add for Senators GM Steve Staios, but they face an uphill climb in their hunt for a playoff spot, especially with Florida and Toronto, two teams outside of the postseason picture in 2026, getting better this summer.
Boxing Day - Saturday, December 26th vs Toronto Maple Leafs
For the first time since 2015, the National Hockey League will hold games on Boxing Day and it's an action-packed slate featuring a total of 11 games including the Montreal Canadiens hosting the Toronto Maple Leafs at the Bell Centre. After being on the road for their first two meetings of the 2026-27 campaign, it'll be the first of two home games for Montreal against Toronto.
This isn't the first time that the two teams have met on Boxing Day. Back in 2009, the Canadiens went out on the road to what used to be known as the Air Canada Center (now Scotiabank Arena) and defeated the Maple Leafs in overtime courtesy of Andrei Kostitsyn.
With the return of NHL games on Boxing Day, many are curious about what the viewership numbers will look like as they go head-to-head with the opening day of the 2027 IIHF World Junior Hockey Championship.
Last game at Saddledome - Thursday, January 28th vs Calgary Flames
In late-January, the Montreal Canadiens will kick off their Western Canadian + Seattle road trip with their last ever stop at the Saddledome in Calgary, Alberta. The Flames are in their final year at the Saddledome before they move to their brand-new arena, Scotia Place, in the fall of 2027.
The Montreal Canadiens organization has some very fond memories of the Saddledome in Calgary. The Canadiens won their penultimate Stanley Cup at the Saddledome back in 1986, which marked the first of Patrick Roy's four Stanley Cups and first of three Conn Smythe Trophies.
Montreal's final game at the Saddledome is set for January 28th at 8 pm ET (6 pm local). After facing the Flames, they'll then head off to take on the Edmonton Oilers on January 30th, Vancouver Canucks on February 1st and Seattle Kraken on February 3rd, before having ten days off for the NHL's All Star break.
Super Bowl Weekend/Ovechkin's last game in Montreal? - Saturday, February 13th vs Washington Capitals
With the NHL hosting the 4 Nations Face-Off in 2025 and returning to the Winter Olympics back in February, the Montreal Canadiens haven't been able to play their traditional matinee back-to-back at the Bell Centre on Super Bowl weekend. That changes this season as they return for the first time since 2024.
The first of the two games will see the Montreal Canadiens take on the Washington Capitals, in what very well could be Alexander Ovechkin's final game in Montreal. After plenty of speculation about his future in the NHL, Ovechkin signed a one-year deal on July 2nd to remain with the Washington Capitals.
Montreal is one of Ovechkin's favourite cities to play in and even said back in 2015 that if he wasn't with the Capitals, he would be with the Canadiens. Montreal Canadiens fans would probably have loved for that to happen, given the fact that Ovechkin has torched the team over his career, recording 44 goals in 63 regular season games.
Brendan Gallagher's return to Montreal - Saturday, March 6th vs Vancouver Canucks
The first Saturday night game in March will be an emotional one for Montreal Canadiens fans as they welcome Brendan Gallagher back to the Bell Centre for the first time since being traded to the Vancouver Canucks in late June.
Gallagher, 34, spent 14 seasons with the Montreal Canadiens, registering 487 points across 911 games, along with 34 points in 79 postseason contests. He was a true leader and a player that every locker room across the National Hockey League needs. While he production may have lacked in certain years, Gallagher never gave up and wore his heart on his sleeve for the entirety of his time as a Montreal Canadien.
Expect a well put together video tribute, which is typically displayed during the first TV timeout in the first period, along with a lengthy standing ovation from fans in attendance at the Bell Centre that night.