How to Bet the NHL Playoffs: Why Stanley Cup Favorites Lose

The NHL playoffs are the place where upsets often happen, the place where the seemingly surefire bets get spoiled. The bottom-line advice for NHL bettors is to proceed with caution.

President’s Trophy Rarely Turns Into Cup

From 2003–25, of the last 22 winners of the NHL's President's Trophy, given to the team with the best regular-season record, only three have gone on to win the Stanley Cup. 

The Washington Capitals pulled off the feat in 2018, but before that, only the 2013 Chicago Blackhawks and the 2008 Detroit Red Wings had done so. Since Washington's title, no Presidents' Trophy winner has converted, including the 2019 Tampa Bay Lightning (swept in the first round), the 2023 Boston Bruins, the 2024 New York Rangers, and the 2025 Winnipeg Jets, all of whom were eliminated before reaching the finals.

In fact, 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. In 2017, the eighth-seeded Nashville Predators swept top-seeded Chicago in the first round and made it to the Cup finals before losing to Pittsburgh.

In 2012, the eighth-seeded Los Angeles Kings won the Cup. In 2006, the eighth-seeded Edmonton Oilers beat Detroit in the first round and went to the seventh game of the Cup finals before losing to Carolina.

Why Stanley Cup Favorites Struggle

There have been several dynasties in the history of the NHL, but in the modern era, it has been elusive. 

The Pittsburgh Penguins and Chicago Blackhawks each won three Stanley Cups from 2009-17, but only Pittsburgh did so in back-to-back seasons. Tampa Bay Lightning also won back-to-back Cups in 2020 and 2021, and the Florida Panthers repeated in 2024 and 2025, but true sustained dynasties remain rare, and prior to Pittsburgh's repeat, back-to-back titles hadn't happened since 1997-'98 Detroit.

Why do favorites so often lose in the NHL playoffs? There are several reasons, not the least of which is that the NHL might have the most parity among all the teams of any league these days. There just hasn't been a lot separating the teams, especially in the salary cap era.

And, as fans of NHL betting sites know, the NHL playoffs are a grueling two-month battle where two teams can play as many as 28 games. Injuries to top players often occur, which can swing momentum in a series.

A hot goalie can single-handedly be the difference in upsets of top teams, such as when Jean-Sebastien Giguere led a lower-seeded Anaheim team to the Cup finals in 2003 or when Dwayne Roloson did it for Edmonton in 2006.

In the NBA, only five to eight guys per team usually have a real say in the outcome of playoff games. In the NHL, 19 guys have roles, and it takes all of them to win a Cup. In the NFL, a quarterback has most of the control, and in baseball, pitchers can often dominate a game.

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 truest team sport.

Other Things To Consider in NHL Playoff Betting

The "Stanley Cup Hangover" seems to zap many teams, though Pittsburgh (2016-17), Tampa Bay (2020-21), and Florida (2024-25) have all managed to repeat in the salary-cap era. 

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 others? 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?

In the end, the NHL playoffs' unpredictability is a big factor in their wider appeal than the regular season—and also why they're so tough to bet on.