What are the can't miss games this season for the Pittsburgh Penguins?

With September upon us, the 2023-24 season is closer than ever for the Pittsburgh Penguins. After a busy offseason full of change, the Penguins are gearing up for a redemption tour to reclaim a playoff spot.

With the roster changes and expectations brewing, this season is shaping up to provide some can't miss matchups for the Boys of Winter. Here are five must watch games this upcoming season.

5. October 11 vs. Chicago Blackhawks

The 2023-24 season starts with an absolute bang for the Penguins, as they take on the Chicago Blackhawks and most recent first-overall pick, Connor Bedard. It's a matchup of one of the greatest of all time versus a player with sky high expectations. It's also the start of a new chapter for the Penguins, as they look to fully turn the page on their first playoff-less season in nearly two decades.

This game will also be the first regular season game Erik Karlsson dons a Penguins uniform, and PPG Paints Arena should be rocking for his debut. 

4. November 19 vs. Vegas Golden Knights

The Penguins welcome the Stanley Cup champs to the Steel City just before Thanksgiving, and it should have all of the makings of a holiday classic.

The Vegas Golden Knights return with a significant amount of the team that won the Cup, but one player they won't be icing is newly acquired Penguins' forward Reilly Smith. The Penguins gave up just a 3rd round pick for the 20+ goal scorer, and he gets a chance to show out against his former team.

3. November 25 vs. Toronto Maple Leafs

Kyle Dubas welcomes the team that fired him mere months ago to his new home arena when the Penguins and Toronto Maple Leafs play for the first time in 2023-24. Both teams went through organizational shakeups this offseason, and the jury is out on what both teams can accomplish in 2024. 

For Dubas, getting a win has to feel personal here. The Leafs put their organizational failures solely on his head when they fired him, and the Penguins are hopeful the Leafs' loss is Pittsburgh's gain. A victory will be a critical cross-division win for the Pens, and a feather in the cap of the Penguins' new front office leader. 

2. January 2 vs. Washington Capitals

When will the battle of giants that is Crosby vs. Alex Ovechkin end? The two biggest superstars of the salary cap era both missed the playoffs for the first time since 2006. Their personal rivalry may have evolved into a mutual respect, but these two teams are likely to battle it out for a playoff spot in the powerful Metropolitan Division. The start to the calendar year of 2024 and the march to the playoffs goes through Washington and will be a nationally televised, must-see matchup.

1. March 10 vs. Edmonton Oilers

A late-season matchup against Connor McDavid and the Edmonton Oilers will be a wonderful test for the Penguins. These are two organizations with similar Stanley Cup ambition and a similar level of disappointment over the past few years. They'll play twice one week apart in March, and the March 10 matchup will be the Pensguins' sixth game in 10 days to start the month. 

To add to the stakes of the match, this will be the first game after the NHL trade deadline. Will Dubas add even more throughout the season or at the deadline? It's possible this game will be the debut of any deadline acquisitions, so it'll be an important game for the standings and for team chemistry. 

The Penguins are in store for an exciting season as they try to return to the postseason with a rejuvenated roster. Every game is important, but these five games are the ones you can't afford to miss this upcoming season. 

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