The Most Shocking Stanley Cup Finals Upsets In NHL History

Hockey | 10/30/24

When the stakes are high and the pressure is on, it's the moments of unexpected triumph that forever etch themselves into the annals of sports history. In the NHL Stanley Cup Playoffs, underdogs have defied the odds, stunning the hockey world with their determination and resilience.

Here, we recount the most legendary upsets in playoff lore.

1938 Stanley Cup Finals: The Sub .500 Blackhawks Win The Cup

1938 Chicago Blackhawks
B Bennett/Getty Images
B Bennett/Getty Images

The 1938 Stanley Cup Finals witnessed the remarkable victory of the under .500 Chicago Blackhawks, making it an outstanding achievement. Throughout the regular season, they struggled, but in the playoffs, they displayed incredible resilience and determination.

No moment in their run was more noteworthy than overcoming a 0-2 series deficit against the Montreal Canadiens to claim the Cup.

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1942: The Leafs Rally From 3-0 Down, Beating Detroit

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1942 Toronto Maple Leafs Stanley Cup Champs
Wikimedia Commons
Wikimedia Commons
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The 1942 Stanley Cup Finals will stand out as one of the most memorable and monumental series of defeats in NHL history. The Toronto Maple Leafs, facing a seemingly insurmountable 3-0 deficit against the formidable Detroit Red Wings, orchestrated a remarkable rally to claim the championship.

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Toronto showcased exceptional toughness and determination, winning four consecutive games to secure an astounding comeback victory and etch their names in hockey lore.

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1975: New York Islanders Comeback From 0-3 To Pittsburgh

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1970s New York Islanders goalie Glenn
Bruce Bennett Studios via Getty Images Studios/Getty Images
Bruce Bennett Studios via Getty Images Studios/Getty Images
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The New York Islanders victory over the Pittsburgh Penguins in 1975 was considered a significant upset due to the remarkable deficit they had to overcome. New York fell down 0-3 to Pittsburgh and then won the next four straight.

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Despite being perceived as the underdogs compared to the talent level of the Penguins, the Islanders showcased their determination and skill, mounting an impressive comeback that showcased their ability to overcome adversity.

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1981: Minnesota North Stars Sweep Boston Bruins

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1980 Minnesota North Stars
Frank Lennon/Toronto Star via Getty Images
Frank Lennon/Toronto Star via Getty Images
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The 1981 Minnesota North Stars' sweep of the Boston Bruins stands as a remarkable achievement in NHL Stanley Cup Playoff history. After barely making the playoffs and finishing third in their division, the North Stars defied the odds by dominating the Bruins in a four-game sweep.

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Their unexpected success showcased the unpredictable nature of the playoffs and highlighted the team's unmatched will and grit.

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1982: Los Angeles Kings Win Over Edmonton And The "Miracle On Manchester"

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1981:  Marcel Dionne of the Los Angeles Kings
Bruce Bennett Studios via Getty Images Studios/Getty Images)
Bruce Bennett Studios via Getty Images Studios/Getty Images)
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In the 1982 "Miracle on Manchester," the Los Angeles Kings overcame a 5-0 deficit to defeat the Edmonton Oilers in a stunning NHL playoff comeback for the ages.

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It remains a monumental upset due to the incredible comeback and the Oilers' dominant regular season performance, making it an unforgettable moment in hockey history.

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1986: Calgary Ends Edmonton's Stanley Cup Dynasty Run

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1986 Calgary Flames
Bruce Bennett Studios via Getty Images Studios/Getty Images
Bruce Bennett Studios via Getty Images Studios/Getty Images
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After losing the series to their bitter rivals Calgary in 1986, the Edmonton Oilers regrouped and bounced back the following year, winning their fourth Stanley Cup in five seasons.

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Led by their star players, including Wayne Gretzky and Mark Messier, the Oilers continued to dominate the NHL, raising Lord Stanley's mug for a fifth time in 1990.

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1993: Los Angeles Kings, Led By Gretzky, Best The Calgary Flames

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Wayne Gretzky 1993 Los Angeles Kings
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Andrew D. Bernstein/Getty Images
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In 1993, the Los Angeles Kings stunned the hockey world by defeating the Calgary Flames in the first round.

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Their remarkable playoff run took them all the way to the Stanley Cup Final, where they faced the Montreal Canadiens. The series against Montreal lasted five games, ending with the Canadiens as the champions.

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1993: New York Islanders End The Pittsburgh Penguins Chances Of Three-Peating

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1993 New York Islanders
Bruce Bennett Studios via Getty Images Studios/Getty Images
Bruce Bennett Studios via Getty Images Studios/Getty Images
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The 1993 New York Islanders achieved a stunning upset by defeating the formidable Pittsburgh Penguins, denying them a chance to claim a remarkable third consecutive Stanley Cup.

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Against all odds, the Islanders triumphed with exceptional skill and determination, securing their place in hockey history and leaving the Penguins shocked and disappointed.

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1994: San Jose Beats Detroit In First-Ever Playoff Series Win

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1994 San Jose Sharks
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Graig Abel/Getty Images
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The San Jose Sharks' series victory in 1994 marked one of the biggest upsets in NHL Stanley Cup Playoff history. It was the first-ever series win for the Sharks, who had entered the NHL in 1991.

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After three years of perseverance, they triumphed over the heavily favored Detroit Red Wings in what can only be described as jaw-dropping.

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1996: Florida Panthers Triumph Over Pittsburgh In The Eastern Conference Finals

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Jody Hull  Florida Panthers 1996
Zoran Milich /Allsport/Getty Images
Zoran Milich /Allsport/Getty Images
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During the 1996 NHL Stanley Cup Playoffs, the Florida Panthers triumphed over the Pittsburgh Penguins in the Eastern Conference Final.

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Following their victory, the Panthers advanced to the Stanley Cup Final and did battle against the Colorado Avalanche. However, the Avalanche proved to be a formidable opponent, defeating the Panthers in a four-game sweep.

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1998: Ottawa Senators Go To Round Two After Beating New Jersey

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Alexei Yashin
Craig Melvin /Allsport/Getty Images
Craig Melvin /Allsport/Getty Images
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The 1998 NHL Stanley Cup Playoffs witnessed a monumental upset as the Ottawa Senators toppled the powerhouse New Jersey Devils in the first round.

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However, despite their inspiring victory, the Senators were not able to sustain their momentum, falling short in the next round and failing to advance further in the 1998 playoffs.

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2002: Carolina Hurricanes Prove Disastrous For The New Jersey Devils

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2002 Carolina Hurricanes
Dave Sandford/Getty Images/NHLI
Dave Sandford/Getty Images/NHLI
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In the 2002 NHL playoffs, the Carolina Hurricanes achieved a remarkable upset by eliminating the New Jersey Devils in the Eastern Conference Final. The Hurricanes displayed impressive performance and determination.

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However, they fell short in the Stanley Cup Final, losing to the Detroit Red Wings. Nonetheless, their unexpected journey captivated fans and showcased their resilience.

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2003: Anaheim Proves To Be Too Mighty For Detroit

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2003 Mighty Ducks of Anaheim
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Jeff Gross/Getty Images
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In a truly epic series, the 2003 Mighty Ducks of Anaheim shocked the hockey world by defeating the powerhouse Detroit Red Wings in the first round of the Stanley Cup Playoffs. The Ducks' triumph over the defending champions showcased their tenacity and sparked excitement throughout the league.

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Although they ultimately fell short, the Ducks advanced to the Stanley Cup Final, where they faced the New Jersey Devils, pushing the more-talented Devils to seven games before losing the series.

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2003: Minnesota Wild Eliminate The Favored Colorado Avalanche

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Minnesota Wild
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Elsa/Getty Images
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The 2003 Minnesota Wild's elimination of the favored Colorado Avalanche was a stunning upset, ending the Avalanche's successful dynasty. Colorado boasted a stellar lineup featuring future Hall of Famers like Joe Sakic, Peter Forsberg, and Rob Blake.

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Their previous accomplishments, including two Stanley Cup victories in 1996 and 2001, amplified the shock of their defeat to the Wild.

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2004: Calgary Flames Beating Detroit In Round Two

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Jarome Iginla
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Jeff Vinnick/Getty Images
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During the 2004 Stanley Cup Playoffs, the Calgary Flames, considered underdogs, stunned the Detroit Red Wings in the second round.

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Their impressive performance propelled them to the final, where they faced the Tampa Bay Lightning. However, the Flames ultimately succumbed to the Lightning in a hard-fought series that went all the way to seven games.

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2012: New Jersey Devils Step Over Philadelphia To The Stanley Cup Final

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Ilya Kovalchuk #17 of the New Jersey Devils
Andy Marlin/NHLI via Getty Images
Andy Marlin/NHLI via Getty Images
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In the 2012 NHL Stanley Cup Playoffs, the New Jersey Devils stunned the Philadelphia Flyers in the Eastern Conference Semifinals. This defeat is considered one of the biggest upsets in Stanley Cup Playoffs history due to the Flyers' strong regular season performance.

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Regardless, the Devils failed to fulfill what appeared to be their destiny, losing in the final against the Los Angeles Kings in six games.

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2006: Edmonton Oilers Topple The Mighty Red Wings

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Jason Smith of the 2006 Edmonton Oilers
Harry How/Getty Images
Harry How/Getty Images
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One of the biggest upsets in NHL Stanley Cup Playoffs history occurred in 2006 when the eighth-seeded Edmonton Oilers stunned the heavily favored Detroit Red Wings in the first round.

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Although Las Vegas oddsmakers had Edmonton as the underdogs, the Oilers managed to defeat the Red Wings in six games. In an impressive playoff run, the Oilers advanced all the way to the Stanley Cup Finals but gracefully bowed out, losing to the Carolina Hurricanes in a hard-fought seven-game series.

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2010: Montreal Canadiens Sent Washington Home Early

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2010 Montreal Canadiens
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The 2010 NHL Stanley Cup Playoffs witnessed a major upset when the eighth-seeded Montreal Canadiens surprised the hockey world by defeating the top-seeded Washington Capitals in the first round.

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This upset was particularly notable as the Capitals had an outstanding regular season. The Canadiens continued their impressive playoff run, advancing to the Eastern Conference Finals, where they eventually lost to the Philadelphia Flyers in a hard-fought five-game series.

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2010: Philadelphia Flyers Rising From The Ashes Of 3-0 To The Boston Bruins

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2010 Philadelphia Flyers
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Al Bello/Getty Images
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In 2010, NHL fans saw the Philadelphia Flyers stage a remarkable comeback against the Boston Bruins in the Eastern Conference Semifinals, erasing a 0-3 series deficit. This feat was highly impressive due to its rarity and the resilience displayed by the Flyers.

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Like all good things, Philly's playoff run ended when they were eventually eliminated by the eventual Stanley Cup champion, the Chicago Blackhawks, in the Stanley Cup Finals.

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2011: Tampa Bay Lightning First-Round Win Over Pittsburgh

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2011 Tampa Bay Lightning
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In the 2011 NHL Stanley Cup Playoffs, the Tampa Bay Lightning embarked on an impressive run by eliminating the Pittsburgh Penguins in the first round.

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The Tampa Bay Lightning's magnificent playoff journey ended in the Eastern Conference Finals with a defeat against the eventual Stanley Cup champions, the Boston Bruins, concluding their playoff campaign.

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2011: Vancouver Canucks Coughing Up A 2-0 Lead To Boston

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Vancouver Canucks
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Harry How/Getty Images
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The 2011 Vancouver Canucks' devastating playoff loss to the Boston Bruins in the Stanley Cup Final remains one of the worst collapses in NHL history.

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Leading the series 2-0 and 3-2, the Canucks' talented lineup couldn't secure victory, causing a shocking upset that left fans, analysts, and the whole hockey world stunned.

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2012: Phoenix Coyotes Send Chicago Home In Round One

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Phoenix Coyotes
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Jeff Gross/Getty Images
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In the 2012 Stanley Cup Playoffs, the Phoenix Coyotes made a remarkable playoff run, emerging victorious in the opening round against the Chicago Blackhawks in a six-game series.

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Unfortunately, their Cinderella story came to an abrupt end. Phoenix faced the eventual Stanley Cup champions, the Los Angeles Kings, losing in five games during the Western Conference Finals.

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2013: Detroit Red Wings Improbable Win Over Anaheim

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2014 NHL Winter Classic
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Dave Sandford/NHLI via Getty Images
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The 2013 NHL Stanley Cup Playoffs witnessed one of the league's biggest upsets when the Detroit Red Wings toppled the Anaheim Ducks in the first round.

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In spite of their strong regular season, the Ducks were eliminated by the Red Wings in a surprising seven-game series, ending their playoff run prematurely.

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2014: Los Angeles Kings Roar Back From 0-3 To San Jose

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2014 Los Angeles Kings
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The Los Angeles Kings' comeback victory over the San Jose Sharks in the 2014 NHL Stanley Cup playoffs is considered one of the worst playoff losses in history. After trailing 0-3 in the series, the Kings made an unprecedented recovery, winning four consecutive games to advance.

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In the finals, they defeated the New York Rangers in five games to secure the championship.

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2014: Montreal Canadiens Wave "Au-Revoir" To Boston

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2014 Montreal Canadiens
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The Montreal Canadiens' triumph over the Boston Bruins in the 2014 Stanley Cup Playoffs Eastern Conference Semifinals is considered one of the league's greatest upsets. The Canadiens advanced past the Bruins in a thrilling seven-game series.

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Montreal was subsequently eliminated in the Eastern Conference Finals after six games by the New York Rangers, the eventual champions.

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2016: Nashville Predators Send Anaheim Golfing

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2016 Nashville Predators
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In a surprising turn of events, the 2016 Nashville Predators defeated the Anaheim Ducks in the first round, defying all expectations. The series was a grueling seven-game battle, lasting longer than anticipated.

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Still, the Predators' playoff journey was short-lived, lasting until they bowed out in a second-round loss against the San Jose Sharks.

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2017: Nashville Predators Bounce The Blackhawks

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2017 Nashville Predators
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The history of Stanley Cup Playoffs is replete with stunning upsets, and one such remarkable moment occurred in 2017. The Nashville Predators, considered underdogs, defied expectations by ousting the formidable Chicago Blackhawks in the first round.

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Nashville continued their impressive run, advancing all the way to the Stanley Cup Final before eventual elimination at the hands of the Pittsburgh Penguins in six games.

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2019: Columbus Blue Jackets Sweep-Away Tampa Bay

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2018 Columbus Blue Jackets
Patrick McDermott/NHLI via Getty Images
Patrick McDermott/NHLI via Getty Images
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The Columbus Blue Jackets 2019 playoff upset of the Tampa Bay Lightning was a monumental achievement due to Tampa Bay's extraordinary regular season record of 62 wins and 128 points, making them one of the most dominant teams in NHL history.

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In contrast, Columbus finished with 97 points, highlighting the magnitude of their unexpected victory.

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2019: St. Louis Blues Stanley Cup Win Over Boston

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2019 St. Louis Blues
Elsa/Getty Images
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The 2019 St. Louis Blues' Stanley Cup victory was a remarkable upset. As the third-place team in their division, they defied expectations in every round of the playoffs.

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They overcame the Winnipeg Jets, Dallas Stars, and San Jose Sharks as underdogs before defeating the favored Boston Bruins in the final, completing their Cinderella story.

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2023: Florida Panthers Oust The Bruins And Their Record-Setting Season

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2023 Florida Panthers
Bruce Bennett/Getty Images
Bruce Bennett/Getty Images
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In a stunning turn of events in the 2023 NHL playoffs, the Florida Panthers achieved a remarkable upset by eliminating the powerhouse Boston Bruins in the first round. The Bruins had an exceptional regular season, tying the NHL record for most wins with 65 and setting a new record for the most points, surpassing the previous mark set by the Montreal Canadiens in the 1976-77 season.

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Florida made it to the Stanley Cup Finals and lost five games to the Las Vegas Golden Knights.