Ten Key Games Of The 2025-26 NHL Season

With much of the NHL offseason already over, fans are beginning to look towards the upcoming season. Fortunately for them, the full slate of scheduled games has been officially released. Every game matters in the NHL from opening night to the final game. However, some games have key matchups and are getting much of the spotlight. 

Chicago Blackhawks @ Florida Panthers: October 7th, 2025

This matchup is the first game of the season, and quite an important one. Connor Bedard and the Blackhawks face the reigning back-to-back Stanley Cup champions in the Florida Panthers. In Florida, this will be a test of Bedard’s greatness as well as the first of three games this night. With the first puck dropping at 5 p.m. EST, it beats a Pittsburgh Penguins away matchup versus the New York Rangers beginning at 8 p.m. EST and the Los Angeles Kings hosting the Colorado Avalanche beginning at 10:30 p.m. EST as the first games of the NHL season.

New York Islanders @ New York Rangers: November 8th, 2025

Not only is the Islanders-Rangers rivalry one of the fiercest in the league, but rookie Matthew Schaefer's involvement makes this game extra important. Schaefer was the first draft pick of the 2025 NHL Draft. Drafted by the Islanders with the first overall pick, a position the Islanders had a slim 3.1% chance of getting, Schaefer has a high likelihood of being on the Islanders roster during the majority of his rookie season. Macklin Celebrini, the first selection of the 2024 NHL Draft, was a standout player for the San Jose Sharks in his first season. This only heightens expectations for Schaefer. 

Nashville Predators vs Pittsburgh Penguins: November 14th and 16th, 2025

These two matchups will be played overseas, specifically in Sweden. Overseas NHL games seem to be becoming more of a commodity in today’s league. This follows the footsteps of the NFL, the NBA, and the MLB. These leagues have all had numerous recent games played outside the United States and Canada, helping to establish these North American sports leagues as more of a worldwide phenomenon. The NHL is hoping for similar success, and it wouldn’t hurt for Swedish superstar Erik Karlsson of the Penguins to be in uniform for this duo of games.  

Edmonton Oilers @ Florida Panthers: November 22th, 2025

A rematch of the 2025 Stanley Cup Finals, which was itself a rematch of the 2024 Stanley Cup Finals, presents many questions that will be asked leading up to this game. Many will wonder who Edmonton’s goalie during this Stanley Cup rematch will be. Others will wonder how both teams will fare in this game and throughout the whole season. Some are curious if Florida can make history by winning the Stanley Cup again this season. These questions will be answered throughout this season, and this game is undoubtedly a match to highlight on calendars. 

New York Rangers @ Florida Panthers: January 2nd, 2026

Each Winter Classic is a key game in the NHL, and this is no exception. The Rangers, under new coach Mike Sullivan, understandably have plenty of expectations this season after the late-season collapse that occurred in the 2024-25 Rangers season. Sullivan, a two-time Stanley Cup Champion as a coach, hopes to hoist the cup with a new team. A game against one of the most dominant teams of the modern era is sure to be a test of Sullivan and the Rangers.

Winnipeg Jets @ Chicago Blackhawks: January 19th, 2026

The fact that Jonathan Toews is playing games at all is worth noting. He signed a one-year contract with Winnipeg after sitting out the last two seasons due to a variety of health issues. However, his return to Chicago, where he captained three Stanley Cup teams and established his reputation as one of the best centers of his generation, is the big one. On nights like that, even beloved superstars can get a mixed reaction. It will be interesting to see Chicago’s reaction to the return of Toews. 

Vegas Golden Knights @ Toronto Maple Leafs: January 23rd, 2026

This game marks Mitch Marner’s return to Toronto. Mitch Marner left the Toronto Maple Leafs, where he had spent his entire NHL career up to this point, to go to the Vegas Golden Knights in a sign-and-trade deal. Vegas signed Marner to a $96 million contract for eight years, then traded Nicolas Roy to the Maple Leafs. Marner had quite a career in Toronto, having been a key player for the franchise for the past nine years. Marner, in his stint with the Maple Leafs, has been named to the NHL All-Star Team twice, has the fifth most points in Toronto franchise history, and the fourth most assists in Maple Leafs history. Nicolas Roy has spent the last six seasons in Vegas and will play against them while in Toronto for this game. While one could expect Toews to be cheered in Chicago, do not expect Marner to get nearly the same treatment in Toronto. 

Boston Bruins @ Tampa Bay Lightning: February 1st, 2026

The NHL’s Stadium Series is important alongside the Winter Classic. In this season, the Stadium Series has the Boston Bruins going up against the Tampa Bay Lightning. While the Winter Classic of the New York Rangers against the Florida Panthers is in LoanDepot Park in Miami, the Stadium Series is in Raymond James Stadium in Tampa. Both key games continue to establish the domination that the state of Florida has in the world of hockey. What is also important to note is that this is one of the last NHL games before the NHL goes on break for the 2026 Winter Olympics, where NHL players have been permitted to participate.

Pittsburgh Penguins @ Washington Capitals: April 12th, 2026

A Penguins-Capitals matchup, for the last two decades, was one of the best matchups in the NHL. Intense playoff games, both teams being in the same region and the same division, and superstars on both teams meant fans could always rely on these franchises for great on-ice games. With guys like Evgeni Malkin, Kris Letang, Alex Ovechkin, and Sidney Crosby getting older, the last Penguins-Capitals game of the season may mean the last Penguins-Capitals game in any of these excellent careers. If any of these players retire, it will be sad to see them leave the rink, no matter the great memories of seeing either team win games in the regular season and the playoffs.

As the puck prepares to drop on a brand-new NHL season, anticipation builds not just for the familiar rhythm of game nights but for those electrifying moments that define the year. This includes the rivalry clashes, the star-studded showdowns, and the playoff-positioning battles that will inevitably unfold. While every game carries weight in the race for the Stanley Cup, certain matchups loom larger, promising intensity, narrative, and unforgettable drama. Fans would be wise to circle those dates on their calendars now. In a league where momentum can shift in a single period and legends are born in overtime, these marquee games could very well shape the destiny of the entire season.