It's already time to start thinking about the 2028 Winter Classic. Yes, I'm aware that the2026 Winter Classic, set to be played on January 2nd between the Florida Panthers and the New York Rangers, has yet to take place. Yes, I'm aware that nothing has been confirmed about the 2027 edition of the game.
But as surprising as it may sound, there might just be far more details available about the 2028 Winter Classic than the 2027 edition.
In October, NHL commissioner Gary Bettman noted the possibility of organizing the 2028 Winter Classic with Buffalo in mind. This comes as the 2028 edition of the game is set to be its 20th anniversary, with Buffalo playing host to that original edition of the Winter Classic at Highmark Stadium (then known as Ralph Wilson Stadium).
If Buffalo is named the host of the 2028 game, the new Highmark Stadium will undoubtedly be the chosen venue. The new home stadium for the NFL's Buffalo Bills is set to be opened in the summer, with the old venue set to host its final Bills home game this weekend.
Should Buffalo be chosen to host the Winter Classic on its 20th anniversary, the league would have a couple matchup options to explore. Let's take a look at some of the more likely possibilities.
Buffalo Sabres vs. Pittsburgh Penguins
With the 20th anniversary of the Winter Classic potentially being staged in Buffalo, why not return to the matchup that started it all: the Buffalo Sabres vs the Pittsburgh Penguins.
That first Winter Classic matchup would pull well over 70,000 fans into a snowy Ralph Wilson Stadium to watch the Buffalo Sabres take on the Pittsburgh Penguins. Sidney Crosby and the Penguins would eventually be the victors, with the legendary Penguin winning the game for Pittsburgh in a shootout.
Outside of that 2008 matchup, the Pittsburgh Penguins would appear in the 2011 and 2023 editions of the Winter Classic, losing to the Washington Capitals and Boston Bruins respectively.
A return to the Winter Classic's inaugural matchup would be a fitting tribute to the game's debut. And should Sidney Crosby remain a member of the Pittsburgh Penguins to that point, it could serve as a meaningful component of a potential farewell tour.
Buffalo Sabres vs. Toronto Maple Leafs
In terms of a popular matchup, this one would probably take the cake.
Maple Leafs fans are already well-known for invading road arenas, and the Buffalo Sabres' KeyBank Center is no exception (the arena is a mere two hour drive from downtown Toronto). So why not give Leaf fans the chance to invade the new home of the Buffalo Bills?
It's a chance that they would surely relish, especially considering that the last time the Leafs were in the Winter Classic was back in 2014, when they defeated the Detroit Red Wings in a shootout.
A Sabres-Leafs Winter Classic at the new Highmark Stadium would not only help to fuel a longstanding division rivalry, but it would also be a chance to deliver it to a national audience.
Buffalo Sabres vs. Ottawa Senators
I understand that the Ottawa Senators might not exactly be the first choice when it comes to the NHL picking an opponent for a potential Buffalo Winter Classic, but there is a little bit of reasoning to justify such a choice.
For one, only half of the league's thirty-two teams have ever taken part in a Winter Classic (that number will rise to seventeen when the Florida Panthers make their Winter Classic debut in 2026). One of the fifteen teams that won't have played in the Winter Classic following this years edition: the Ottawa Senators.
That said, you could make that same argument for the Sabres to play any of the other four Canadian franchises (Vancouver Canucks, Edmonton Oilers, Calgary Flames, Vancouver Canucks) that have not played in the cornerstone of the league's outdoor presence.
However, past editions of the Winter Classic have typically focused on division rivalries, teams in close proximity of one another, or other teams that have a significant rivalry with the host of a given Winter Classic. Ottawa fills two of those criteria; not only do the Senators play in the same division as Buffalo, but Ottawa is just a six-hour drive from Buffalo.
Add on the fact that the Sabres and Senators recently swapped star players (Josh Norris was exchanged for Dylan Cozens as part of a trade conducted during the 2024-25 season), and you have the ingredients for a workable Winter Classic matchup between the Buffalo Sabres and the Ottawa Senators.
Buffalo Sabres vs. Chicago Blackhawks
If a 2028 Winter Classic is going to be a celebration of the game's 20th anniversary, why not invite the team that has played in the game most often: the Chicago Blackhawks.
Of the sixteen (soon to be seventeen) teams that have participated in the Winter Classic, Chicago leads the way with five total appearances in the game (Boston is second with four total appearances). And funny enough, the Blackhawks have never once won the Winter Classic.
In terms of intrigue, a Sabres-Blackhawks Winter Classic would highlight two of the league's more up-and-coming franchises; the Sabres are currently enjoying a nine-game win streak that has catapulted them firmly into playoff contention, while the Blackhawks recently enjoyed one of their stronger starts to the season.
With both franchises set to be in position to be key players in the future, a Winter Classic encounter would be a reasonable means to promote these two emerging teams.