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Top 10 Underdogs To Win the Stanley Cup

With the Stanley Cup Final starting on Wednesday between the Avalanche and the Lightning, NHL handicapper Jason Yamaguchi ranks his top underdogs to ever win the Stanley Cup.
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Top 10 Underdogs To Win the Stanley Cup

This year's iteration of the NHL playoffs has resulted in a Cup Final series between the Tampa Bay Lightning and the Colorado Avalanche, two of the league's elite teams. In fact, at the beginning of the season, many predicted that these would be the two squads to represent their respective conferences in the finals. Those predictions made a lot of sense — Tampa had just won their second straight Stanley Cup, and Colorado had been in the competitive mix for years.

However, it's actually relatively rare to see the two best teams in the NHL face off in the finals. Given the relative parity of the league combined with the difficulty of winning three straight playoff rounds (let alone four), there is often a surprise team that reaches the final round. Following that line of reasoning, let's take a look at the biggest underdog stories of the past regarding teams that won it all in the NHL.

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10. 1997 Detroit Red Wings

The 1997 Red Wings would go on to win the first of three Stanley Cups in six years for their franchise, but, much like many other prospective dynasties, they were not initially viewed as a powerhouse. They were underdogs by a huge margin in the Conference Finals against the Presidents' trophy-winning Avalanche (-240), and were also given long odds against the Flyers in the Cup Final. Despite the doubt from the oddsmakers, Detroit dispatched Colorado in six and swept Philadelphia en route to their first Cup since 1955.

9. 1991 Pittsburgh Penguins

Despite having an all-time great in Mario Lemieux and a budding superstar in Jaromir Jagr, these Penguins were not among the Cup favorites heading into the playoffs. Five teams finished with 100 or more points; Pittsburgh, by virtue of their 41-33-6 record, had just 88. However, a combination of resilient play and lucky matchup breaks (the 68-point North Stars making the finals, for one) brought Pittsburgh its first Stanley Cup.

8. 2011 Boston Bruins

Led by the magical play of the late-blooming Tim Thomas, the Bruins managed to win their first Stanley Cup since 1972. Boston had a high-caliber team, but they were not expected to defeat Vancouver in the Cup Final. The Canucks had won the Presidents' trophy by a significant margin, boasting a league-best record of 54-19-9. As a result, they were -250 favorites for the series against the Bruins. However, Boston pulled out the victory, including a 4-0 road win in Game 7.

7. 1990 Edmonton Oilers

Many assume that this Oilers squad was a continuation of the dynasty that had netted them three Cups in the prior five years, but that was not the case. Due to financial reasons and player discontent, Edmonton had traded away multiple superstars who had been present for their other Cup runs. Among those names were Wayne Gretzky and Paul Coffey — you may have heard of them. Still, the 1990 Oilers managed to win it all, including a sweep of the heavily favored (-220) Bruins in the Stanley Cup Final.

6. 2018 Washington Capitals

The 2018 Capitals' Cup run isn't really considered a Cinderella run, but perhaps it should be. The team overcame long odds to win their first Stanley Cup in franchise history, winning three straight series in which they were not favored. In two of those series, the discrepancy in odds was significant — the Lightning were -200 favorites in the Eastern Conference Finals (WSH won in 7), and the Golden Knights were -150 favorites in the Cup Final (WSH won in 5). In other words, this Washington squad overcame exceedingly difficult matchups to win the Cup, a fact that should not be overlooked.

5. 1980 New York Islanders

The '79-80 Islanders won the first of four straight cups for the franchise, but you wouldn't have guessed it from this team's performance in the regular season. The Islanders finished the season with a record of 39-28-13, leaving them with just 91 points. However, they entered the playoffs on a hot run, and the momentum carried them through the playoffs. During their Cup run, they won three straight series in which they were heavy underdogs, defeating the Bruins (who finished with 105 points), the Sabres (110 points), and the regular-season champion Flyers (116 points).

4. 2006 Carolina Hurricanes

Following the 2005 lockout, the Hurricanes entered the following season with 60-1 Cup odds, tied for the second-longest in the league. They had a strong regular season—finishing second in the Eastern Conference—but still had to battle tooth and nail to win four rounds in the playoffs. To this day, that team stands as Carolina's only championship squad in franchise history.

3. 1995 New Jersey Devils

Despite being an overtime goal away from the finals in 1994, the Devils had a mediocre regular season during the following year, going 22-18-8. However, that performance had no bearing on their quality of play in the playoffs. New Jersey toppled three higher seeds in the first three rounds, losing just four games during those three series. That set up a matchup in the finals with the Detroit Red Wings, who had won the Western Conference with ease after attaining the NHL's best regular-season record. The Devils paid no mind to the fact that they were massive underdogs, sweeping the Wings (-250) for their first Stanley Cup.

2. 2012 Los Angeles Kings

The 2012 Kings squeaked into the playoffs as the Western Conference's eighth seed, meaning that they began the playoffs as significant underdogs. However, they made quick work of the conference, winning their first three rounds in five, four, and five games to set up a matchup with the Devils in the Cup Final. LA defeated New Jersey in six games for the franchise's first-ever Stanley Cup.

1. 2019 St. Louis Blues

On January 3rd, 2019, St. Louis had the fewest points of any team in the NHL. Powered by the stellar play of rookie goaltender Jordan Binnington and the defensive overhaul enacted by (then interim) head coach Craig Berube, the Blues went on an improbable run that allowed them to snag a playoff spot. 16 wins later, including a Game 7 victory on the road against the Bruins, the Blues were crowned as the Stanley Cup champions. Their season represents one of the most remarkable turnarounds in sports history.


Jason Yamaguchi is an avid New York sports fan. He has a proven record of providing +EV bets by combining traditional handicapping tactics with advanced statistics. You can follow him on Twitter @TopMoneyPicks to view all of his bets, including NFL, NHL, and MLB picks.


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