Ranking Potential NHL Conference Finals and Stanley Cup Matchups

  • We look ahead at the most entertaining matchups still to come in the Stanley Cup Playoffs
  • The Boston Bruins and Montreal Canadiens could square off in an ‘Original Six’ Cup Final
  • Colorado, the top team in the NHL regular season, could face the reigning champions in Tampa Bay

This year, the traditional Eastern Conference champion vs. Western Conference champion format is out the window. Instead, the four teams that advance to the 2021 Stanley Cup Semifinals will be re-seeded based on their regular season point totals and placed into a new 1 vs. 4 and 2 vs. 3 bracket.

Since Colorado and Vegas tied atop the regular season standings, the victor of their second-round matchup will face the winner of the Canadiens/Jets series, as both North Division clubs are the worst teams (by point total) left in the postseason. That leaves the winner of the Hurricanes/Lightning tilt to play whoever advances from the Bruins/Islanders battle.

With that in mind, let’s rank the possible Conference Final and Stanley Cup showdowns from best to worst. But before we start, check out our NHL betting tips page for advice on how to wager on hockey.

Hockey’s Final Four

With the Montreal Canadiens comfortably ahead in their series, could we see a “Patrick Roy Invitational” vs. the Avalanche in Round 3? Just over 25 years ago, the Hall of Fame netminder demanded a trade from the Habs and shortly after landed in Colorado where he won two more Stanley Cups.

The Avs moved from Quebec City to Denver the season before winning the Cup in 1996, so this matchup has some additional history as both clubs originally hailed from the Canadian province of Quebec.

On the other side of the bracket, the teams that face off in the semi-final should be familiar with one another. Tampa Bay defeated the Islanders in the Eastern Conference Final in the bubble last season and beat the Bruins in the second round in both 2018 and 2020.

Should Carolina advance, Rod Brind’Amour’s squad swept Long Island in the second round in 2019 before getting swept themselves by Boston the very next round. The B’s also defeated the Canes in five games last year.

Potential Cup Matchups

While it’s one of the most unlikely, seeing two Original Six rivals like Boston and Montreal in the Stanley Cup Final would be mouthwatering for hockey purists. The series would offer a heavyweight goaltending battle between Carey Price and Tuukka Rask as the underdog Habs would look to hand the Bruins their third Cup Final loss in the past decade.

From a pure hockey standpoint, it might be even better to see the reigning champions in Tampa Bay take on the Avalanche, this year’s President’s Trophy winners.


There certainly would be no shortage of skill on display with Colorado’s talented young core of Nathan Mackinnon, Mikko Rantanen and Cale Maker looking to dethrone Nikita Kucherov, Brayden Point and Victor Hedman and etch their name on Lord Stanley for the first time.

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Steve Dominey

Steve has almost 15 years of experience in marketing, PR and sports television. After acquiring a Journalism degree from Carleton University, he assembled highlight packs for Canada's most-watched sports network (TSN) before transitioning to a career in communications. He describes himself as a good father, great dog owner, and mediocre gambler and husband.