Stanley Cup Playoffs Betting Strategies

It’s death, taxes, and a super-team winning the championship in the NBA. In Major League Baseball, the Yankees, Dodgers, and Red Sox—the big-market teams—usually make it to the end. In the NFL, it’s been Patrick Mahomes and the Chiefs.

The NHL playoffs are where upsets often happen, and seemingly surefire bets get spoiled. Many top-seeded teams have been bounced from the playoffs in the early rounds, and many lower-seeded teams have either won the Cup or advanced to the Finals. That said, the average Stanley Cup winner has been seeded in the Top 3 of its conference since 2000.

On the other hand, only eight teams in NHL history have won the President’s Trophy (given to the team with the best regular-season record) and the Stanley Cup in the same season.

The bottom-line advice for Stanley Cup bettors is to be careful.

Several dynasties have existed throughout NHL history, but they've become rare in the modern era. Why do favorites so often fall short in the NHL playoffs? 

There are a few key reasons:

• Parity: No league today has more parity than the NHL. The talent gap between top seeds and lower-ranked teams is often razor thin, making upsets far more common than in other sports. There hasn’t been much separating the teams, especially in the salary cap era.
• Injuries: The NHL playoffs are a grueling two-month battle in which two teams can play as many as 28 games. Injuries to top players often occur, which can swing momentum in a series.
• Goalie Play: A hot goalie can single-handedly be the difference in upsets of top teams.
• Team Size: In the NHL, 19 guys have roles, and it takes all of them to win a Cup. Fans of the other leagues will argue that their sport is as much a team sport as any other, but hockey probably has the best argument that it’s the most actual team sport.

The “Stanley Cup Hangover” seemed to zap many teams until 2025. The Florida Panthers ended a long drought by winning back-to-back Stanley Cups in 2024 and '25, becoming the first team to repeat since the Penguins in 2016 and 2017. Before that, no team had done it since the Red Wings in 1997 and 1998.

All of the factors listed above are contributors to that, but there are other things to consider when considering bets on the NHL playoffs:

• How was the favored team playing down the stretch of the regular season?
• Did they develop some bad habits?
• How far is the travel between the two cities in a particular matchup? Could it tire out one team more than the other?
• How rabid is the fan base compared to the other? Loud, passionate crowds can often spur teams on, particularly underdog teams.
• How much playoff experience does the goalie of a favored team have? Does the goalie have a history of faltering when the pressure is amped up, or vice-versa?

Ultimately, the unpredictability of the NHL playoffs makes them more compelling than the regular season and challenging to bet on.

There’s no way to bet on the NHL, making it fun. The key is recognizing that each moment brings challenges. What works in the regular season might not fly under the bright lights of a Winter Classic or in a Game 7.

The best approach? Stay flexible, do your homework, and trust your read on the matchup. Because in this league, the only constant is chaos—that’s precisely why we love it.