5 games that stand out on the Chicago Blackhawks' upcoming 2025-26 NHL schedule

The Chicago Blackhawks enter their 100th season with a young, talented roster and a few key games that stand out on the schedule.

This season is all about growth, development, and honoring the past. With a promising young core and exciting matchups on the calendar, Blackhawks fans have plenty to look forward to as the team continues to build for the future and get back in playoff contention.

With that in mind, here are five must-watch matchups for Blackhawks fans during the 2025-26 season.

1. Oct. 11 vs Montreal Canadiens

The Hawks open their season at the United Center against the Montreal Canadiens in an Original Six showdown.

This game brings together two teams with a lot of young talent on both sides: Connor Bedard, Frank Nazar, and 2025 third-overall draft pick Anton Frondell for the Hawks; Cole Caufield, Nick Suzuki, and rising star Ivan Demidov for the Canadiens.

Demidov had an outstanding performance in his NHL debut against Chicago last season, recording a goal and assist in the first 10 minutes of the game.

With the Hawks wearing their new centennial jerseys and fans filling up the United Center, this should be a thrilling night in Chicago.

2. Oct. 28 vs Ottawa Senators

This game is part of the NHL's "Frozen Frenzy," when all 32 teams play on the same day. The event is set to begin on Oct. 28.

The Senators are trying to go from a solid team to a great one, led by Brady Tkachuk and Tim Stutzle. This should be a great matchup between the two teams.

The full-day slate of games will be featured across ESPN and NHL Network.

3. Oct. 30 at Winnipeg Jets

Former Blackhawks captain Jonathan Toews will face his old team for the first time since signing with the Jets.

Toews played 15 seasons with the Blackhawks and led them to three Stanley Cups (2010, 2013, and 2015). In his final season with Chicago (2022-23), he posted 31 points (15 goals, 16 assists) in 53 games.

4. Jan. 1 vs Dallas Stars

This is not a Winter Classic game, but it's still a great way to kick off the new year as the Hawks host the Dallas Stars at the United Center. Even if it were a Winter Classic game, it'd most likely be a loss for the Hawks, considering their 0-5 record in Winter Classic appearances.

5. Jan. 19 vs Winnipeg Jets

This will be an emotional game to watch for Hawks fans during the 2025-26 season. Jonathan Toews will return to the United Center for the first time since leaving Chicago.

Fans can expect a warm welcome, emotional game, similar to the one Patrick Kane received when he returned to Chicago as a member of the Red Wings in the 2023-24 season.