The Toronto Maple Leafs announced their 2026-27 schedule on Wednesday, and with it comes the excitement of the return to hockey being just around the corner.

While every game is always worth tuning in for if you are a fan of the team, some Leafs games are naturally going to get extra brownie points for intrigue above others at the outset. Whether it is due to a certain matchup, a storyline, or the chance at seeing something interesting, there will be some regular-season matches that will get more eyeballs on them than the typical Tuesday night tilt.

We have identified six of those games for the 2026-27 season that are worth marking down on your calendars right now.

The forever rivals in the Leafs and Canadiens will begin their respective campaigns against each other for the seventh consecutive time, and the second straight year that the game will happen in Toronto. Opening night alone is always going to be a big draw as it is the first game of the regular season and the renewed sense of optimism that maybe things will be different for the team this time around.

What gives this game extra intrigue is the fact that it will mark Gavin McKenna’s NHL debut. The number one overall pick of the 2026 NHL Draft brings hope to a fanbase that was in dire straits when the 2025-26 season concluded, given the state of the franchise before their fortunate draft lottery win. While no one is expecting him to light the world on fire in his first game the way Auston Matthews did nearly a decade ago, it will nonetheless be exciting to see what McKenna can do in his maiden voyage as an NHLer. Combine that with it being the debut of the new look roster going up against a Habs team that made it to the Eastern Conference Finals, and this is bound to be a great game to kick off the season.

The intrigue about this matchup is quite obvious: this will be the first time the top two picks of the 2026 Draft face off against each other in the NHL. McKenna and Ivar Stenberg will no doubt be on their A-game and will be the point of focus for the night, with the latter likely extra motivated to show the Leafs faithful what they missed out on.

Beyond that storyline is an intriguing clash between two teams at different stages of their contention window, but both hoping to reach the playoffs. The Sharks boast an exciting young core in Macklin Celebrini, Will Smith, and Sam Dickinson, while the Leafs still have their elite talent in Matthews, William Nylander, and John Tavares. As far as early-season games are concerned, this is easily among the standouts.

Any game between Matthews and Connor McDavid is always going to get extra attention, but this year’s edition adds an extra level of juiciness that will make it appointment viewing as it is Mike Babcock’s first game back in Toronto since November 2019. His exit from the team was quite messy, to put it mildly, and a lot has changed since Babcock last manned the Leafs’ bench, with one of them being that one of his former assistants, Jim Hiller, is now the leading man.

While the earlier matchup in Edmonton on October 24th, the rematch gets the edge purely because of the spectacle that could be in store for Babcock when he comes back to Toronto for the first time in nearly seven years. One has to wonder what the reception will be for him, though it may not be as loud as the one Mitch Marner got in his return last season.

There’s rarely been a dull moment between these two Atlantic Division rivals, especially in recent years with the two meeting up in the second round of the playoffs in 2023 and 2025. So naturally, the first time these two teams face off is going to get some extra attention because there is a good chance that the Panthers are once again the team to beat in the East.

What makes this particular matchup intriguing is twofold. For starters, this will be the first time Sergei Bobrovsky will play against his former team that he helped guide to two Stanley Cup wins. Given how things unfolded with his exit, every subsequent showdown will be his chance to show that they made a mistake letting him go to Toronto. Also, the inclusion of Brady Tkachuk when his brother Matthew has already been a presence in this rivalry is bound to make for some fireworks.

It may seem odd to put the Leafs’ first game against the Ducks here, given that the score was seemingly settled in the last matchup when Radko Gudas and Max Domi fought each other off the opening faceoff in Anaheim. But the previous encounter, when Gudas tore up Matthews’ knee and the Leafs did nothing about it, was a defining moment for the team last season in the worst way and one of the reasons why they have since undergone seismic changes.

Gudas may not be on the team anymore as he was traded to the Panthers, but the Leafs who remain on the team who were present that night can’t forget how poorly they handled things the last time the Ducks were in Toronto. They obviously can’t take back what they did, but they can certainly show in this encounter that they learned from their mistakes by not making it an easy night for Anaheim.

This will be Hiller’s first time back in Los Angeles since he was fired by the Kings, so that alone will give the matchup some extra juice. How the Leafs perform for their new bench boss will certainly be interesting to monitor, as the two visits they made to St. Louis to play the Blues after Craig Berube was hired left a lot to be desired.

Matchups between these two teams of late have been quite entertaining, as evidenced by their most recent encounter towards the end of last season. Add to it all the star power that both teams possess, and this should make for a solid late-night watch on a Wednesday for Leafs fans.

Wednesday, September 30th – Islanders @ Maple Leafs: Matthew Schaefer vs Gavin McKenna will be appointment viewing. Also, this will be Matias Maccelli’s long-anticipated return to Toronto.

Saturday, December 12th – Golden Knights @ Maple Leafs: Here’s hoping the Leafs can put on a better showing for the fans in Marner’s second visit to Toronto as an opponent.

Saturday, January 16th – Penguins @ Maple Leafs: It could perhaps be the last time Sidney Crosby plays against the Leafs in Toronto.

Sunday, March 28th – Capitals @ Maple Leafs: It could perhaps be the last time Alex Ovechkin plays against the Leafs in Toronto.