The Maple Leafs now know the shape of their 2026-27 season, and it starts fast.
Toronto opens the NHL regular season on Tuesday, September 29, at home against Montreal, then turns right around for a back-to-back against the Islanders on Wednesday, September 30. With the league moving to an 84-game schedule and the opener landing at the end of September, the Leafs are suddenly only 75 days away from hockey.
The first stretch is a home-heavy one. Toronto begins with a four-game homestand against Montreal, the Islanders, Ottawa and Nashville before heading west for a Vegas-Colorado-Utah road trip.
There are a few dates that jump off the page. Boxing Day brings a Leafs-Habs matchup in Montreal, while Black Friday features a 1 p.m. game in Boston against the Bruins.
Sergei Bobrovsky’s return to Florida comes late, with Toronto visiting the Panthers on March 6 and April 1. Florida, meanwhile, comes to Toronto first on December 3.
The Leafs will also see a few familiar faces in unusual spots. Daniel Alfredsson and Toronto go to Ottawa for the first time on January 20.
Jim Hiller’s former team, the Kings, come to Toronto on November 19, and the Leafs head to Los Angeles on December 30. Darren Raddysh returns to Tampa on February 20.
There’s also a note on Mike Babcock, who the Leafs will welcome to Toronto on Saturday, November 14, if he makes it through training camp in Edmonton. Toronto visits Edmonton on October 24, so the two meetings with McDavid’s Oilers come early, within the first month and a half of the season.
The schedule also includes two games against the Cup champion Carolina Hurricanes, on Saturday, December 5 and Friday, March 5. The next-gen 1 p.m. game is set for Monday, December 21, against the Washington Capitals.
From a grind standpoint, the Leafs get a lighter load than last season. After dealing with 15 back-to-backs in the Olympics-affected 2025-26 schedule, they’ll have 11 this year.
January looks like a prime opportunity to bank points, with 13 games and a five-game homestand in the middle. March, by contrast, is the heaviest month on the calendar at 16 games. That stretch includes two games each against Florida and Tampa, plus Dallas, but it also comes with a fair share of softer opponents, including Detroit, Seattle, Winnipeg, Vancouver, the Rangers and the Devils.
Toronto’s longest road swing runs from December 22 to January 7, a seven-game trip that lands right through the holidays. The Christmas break does at least split it up a bit.
The All-Star Break falls between January 31 and February 7, and the regular season ends on April 10 at Madison Square Garden in New York after a four-day break. That timing could work well if the Leafs are using the gap to rest and reset for the playoffs.
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What makes the pivot sting is that Torontos level of interest has never been entirely clear, even as Kane lingered as a plausible target. With that door now effectively closed, the Leafs may have to shift to thinner alternatives on the wing, with Eeli Tolvanen among the remaining options worth watching. It is the kind of late-summer turn that can force a team to choose between patience and a move that feels more like settling than solving. [Read more 🡒]
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That bargain is part of what has made Knies such a tricky name to even put in trade conversations. Toronto wants a quick path back to contention, and the wing depth around the roster gives the front office options, but moving a player with this kind of upside and cost control is not a simple decision. The Leafs may have reasons to listen, yet the longer the market keeps resetting upward, the harder it gets to imagine replacing what Knies already gives them. [Read more 🡒]
Matthew Knies Is Starting To Look Like A Massive Leafs Win
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Knies has given the Leafs real value on the ice, too, with a breakout season that showed why the team was comfortable making a long-term bet. As salaries for ascending forwards keep pushing higher, Toronto has to like where it landed with a player who is still trending up and whose deal leaves the club with more flexibility than many of its peers enjoy. [Read more 🡒]