The 2026 Heritage Classic will act as the first of three outdoor hockey games this season is set to take place on Sunday, October 25.
While the Edmonton Oilers will not be involved in the contest, they have a long-standing connection to its history and current iteration.
Let's take a look.
Who's involved in this year's Heritage Classic?
The 2026 Heritage Classic will see the Winnipeg Jets host the Montreal Canadiens at Princess Auto Stadium, typically the home of the CFL's Winnipeg Blue Bombers and U Sports' University of Manitoba Bisons football team.
This will be the second time that Winnipeg has hosted the game.
Have the Oilers been involved in the Heritage Classic?
Yes.
The Oilers have played in the Heritage Classic three times throughout their history, sporting a 2-1-0 record in those contests.
The first time they appeared in the game actually came during the contest's inaugural edition, which saw the Oilers host the Canadiens at Commonwealth Stadium, which is home to the CFL's Edmonton Elks and the occasional national football contest. That game ended in a 4-3 loss for the Oilers.
Their second appearance in the game took place 13 years later, when they travelled to Winnipeg to take on the Jets. The Oilers would go on to defeat the Jets by a 3-0 scoreline.
Seven years later, the Oilers welcomed the Calgary Flames for the 20th anniversary of the Heritage Classic. Not only did the game take place at Commonwealth Stadium once again, but it saw the Oilers reverse the result of that inaugural edition as they defeated their intra-provincial foes in what was a 5-2 decision.
Who has the upper hand this time?
Overall, Montreal's start to the regular season has been middling. Even then, Winnipeg's early momentum has very clearly stalled.
The short and potential long-term impacts of their ongoing run, which has seen them go 0-2-2 over their last four games since starting 4-1-1, is brought further into question when considering the fact that goaltender Connor Hellebuyck was recently traded to the New Jersey Devils. That said, could the trade help the Jets?
After all, Dawson Mercer was a key part of two postseason campaigns for the Devils - he recorded 56 points and a +22 +/- rating during the 2022-23 regular season - while ex-Oiler Nick Bjugstad will act as a veteran depth piece for Winnipeg's forward group.
While the Habs are 4-1-1 in their last five games, it remains to be seen if their performances are truly the most convincing. The goalscoring, which has been an issue at times last spring, has been there for Montreal, especially given that they've scored 32 across their first 10 games.
The goaltending? Not necessarily.
For one, they've given up at least three goals seven times, five of which have seen them concede more than that benchmark. In addition, four of their five wins have either been decided by just one goal or in a shootout.
This idea is also reinforced in a statistical sense. Entering Saturday's action, the Habs are 26th in the league in goals against per game (3.50), they've given up the 12th-most goals in the league (35), and they have the fifth-worst save percentage (.875). That is rectified to an extent by the fact that the Habs give up the 10th-fewest shots against, but not a lot of saves are being made; the team is eighth-from-last in that regard.
Winnipeg is far stronger in that regard. Despite the recent slump, the Jets still give up just below three goals per game, they're tied for the fifth-fewest goals against in the league, and they have the seventh-best save percentage.
The Habs do outscore the Jets by 0.60 goals per game, and they are more efficient when it comes to converting their scoring chances to goals. That said, Winnipeg has the edge on the power play, though the penalty kill is essentially a toss-up between the two teams.
Any former Oilers?
Outside of Bjugstad's arrival, ex-Oilers netminder Stuart Skinner is expected to firmly take the reins of the Jets' goaltending lineup now that Hellebuyck is out of the picture.
No former Oilers are part of this year's Montreal roster.
Prediction: Winnipeg Jets 3, Montreal Canadiens 2
Sometimes, all that a team needs to restart their season is a special occasion.
For the Jets, this comes in two forms.
One is that of the Hellebuyck trade. While there is always the chance that the Jets don't end up coming out of the trade a better team, the removal of the off-ice chaos that surrounded it could yield a more confident hockey team.
The other is the Heritage Classic itself. Sometimes, getting the chance to play outdoor hockey in front of a home crowd that is (at least) double the capacity of a team's arena is enough to motivate a roster to put together a very strong performance.
While home teams are just 4-3 in the Heritage Classic, the hosts are also enjoying a three-game winning streak in the contest. That streak happened to be started by the Jets back in 2019, when they hosted the Calgary Flames at Mosaic Stadium, the home of the CFL's Saskatchewan Roughriders.
With all of the above analysis in mind, I give the slight edge to the Jets. If this becomes a track meet, then that advantage obviously flips to the Canadiens. But if the goaltending remains strong and the Jets can make the most of their opportunities, then Winnipeg has a strong chance to emerge on the right side of this game.
I'm confident enough to say that the Jets will get themselves back on track and start the post-Hellebuyck era 1-0-0.
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