Top 5 Greatest Stanley Cup Playoff Upsets

If history has shown hockey fans anything, then it has illustrated that there are no guarantees when the Stanley Cup playoffs begin. Here are the top five Stanley Cup upsets in hockey history.

Greatest Stanley Cup Upsets #5: 1945 Semifinals

Toronto Maple Leafs vs. Montreal Canadiens

After the end of the 1944-45 regular season, the Montreal Canadiens were the best team in the NHL as they had only lost eight regular season games and finished with a record of 38-8-4 in 50 games played. On the other hand, the Toronto Maple Leafs barely finished above .500 and were not expected to put up much of a fight against a very potent Montreal team.

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Given the fact that the Maple Leafs trailed the Canadiens by almost 30 points in the standings at the end of the regular season, the improbable win by Toronto in the best of seven series was all the more impressive. Toronto’s victory against the league-best 1945 Canadiens illustrated that a team can have a great regular-season record, but the Stanley Cup Playoffs hold a different test for teams that want to be immortalized in hockey lore.

The Stanley Cup. (mastermaq, Flickr)

However, things did not go according to plan for Montreal as the Maple Leafs won the first two games by scores of 1-0 and 3-2, respectively. Montreal managed to win Games 3 and 5, but the Maple Leafs were determined not to let their series lead escape and won Game 6 in Toronto by a score of 3-2. All four victories by the Maple Leafs were by one goal, but the team continued its inspired play when they met the Detroit Red Wings in the Stanley Cup and ousted the favorites in seven games. Frank “Ulcers” McCool continued his consistent regular-season netminding into the 1945 post-season as he and the Maple Leafs surprised Montreal, Detroit, and the hockey world through their determined play in the playoffs.

Given the fact that the Maple Leafs trailed the Canadiens by almost 30 points in the standings at the end of the regular season, the improbable win by Toronto in the best of seven series was all the more impressive. Toronto’s victory against the league-best 1945 Canadiens illustrated that a team can have a great regular-season record, but the Stanley Cup playoffs hold a different test for teams that want to be immortalized in hockey lore.

Greatest Stanley Cup Upsets #4: 1975 Quarterfinals

New York Islanders vs. Pittsburgh Penguins

During the mid-1970s, the New York Islanders were viewed as just another expansion franchise. That label would be removed by the end of the Isles’ playoff run in 1975 as the team beat their crosstown rivals (New York Rangers) in a three-game preliminary round and had two more memorable rounds with the Penguins and Flyers afterward.

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Glenn ‘Chico’ Resch (New York Islanders / NHL, Wikimedia Commons)

After a hard-fought series against the Rangers, the Islanders looked as though they had run out of gas against the Penguins as Pittsburgh took Games 1, 2, & 3 by scores of 5-4, 3-1, & 6-4, respectively. Even though Billy Smith would have a wonderful career in the NHL and with the New York Islanders, Glenn “Chico” Resch was the reason for the Isles’ comeback. Resch stepped in for an ineffective Smith and promptly won Games 4, 5, 6, and 7, allowing only 4 goals against in those contests.

Game 4 in Long Island was most certainly a pressure cooker for Resch and the team as the Nassau Coliseum faithful chanted, “Chico! Chico!”, in a packed house elimination game, but Game 7 of the series had to be one of the best games played in the series. Chico Resch’s best friend helped him out three times in the opening minutes of Game 7 and Ed Westfall sealed the Penguins’ fate by scoring the only goal of the contest during the late stages of the third period.

The most interesting part about this feat was that it hadn’t been done since the 1942 Maple Leafs came back from a 3-0 Stanley Cup Finals deficit to the Red Wings. After the Islanders beat the Penguins in such a fashion, almost 30 years would pass before another professional sports team (2004 Boston Red Sox) accomplished such a comeback. Even though Chico Resch would eventually leave Long Island, the netminder’s heroics in the 1975 playoffs cemented his status as an Islander legend and helped put the expansion franchise on the map in a big way.

The Islanders earned the number nine spot over the Maple Leafs because of the inexperience of the franchise (three years old) and the difficulty of the comeback. Even though it doesn’t get much harder than coming back from a 3-0 series deficit in the Stanley Cup Finals, the New York Islanders had to complete their comeback on the road against Pittsburgh after they had been dominated in the first three games of the series. While the Isles wouldn’t win a Stanley Cup for several years, their Stanley Cup upsets against the Penguins had some very positive outcomes in the long run for a young and developing organization.

Greatest Stanley Cup Upsets #3: 2003 Western Conference Quarterfinals

Minnesota Wild vs. Colorado Avalanche

The 2002-03 Minnesota Wild were a very defensive-oriented team as head coach Jacques Lemaire was one of the biggest proponents of the trapping system. On the other hand, the Colorado Avalanche were an offensive powerhouse with Hall of Fame goalie Patrick Roy manning the team’s crease.

After winning Game 1 on the road, Minnesota dropped three straight against the Avalanche and things looked pretty grim for the Wild. However, the Wild were able to pull out three straight victories by the score of 3-2 as overtime heroics from players such as Andrew Brunette and Richard Park allowed Minnesota to come back from a 3-1 series deficit and bump the number-three seeded Avs. Many didn’t give the Wild a chance after losing three straight games to the Avalanche, but Minnesota proved many naysayers wrong through some hard work and grit as the team had to win two road games in Colorado in order to advance to the Conference Semifinals.

Patrick Roy, stanley cup upsets
Patrick Roy. (Steve Babineau/NHLI via Getty Images)

Minnesota’s 2002-03 playoff berth was its first since its inception into the NHL as an expansion franchise, but the Wild made the most of their trip. The goalie tandem of Manny Fernandez and Dwayne Roloson helped Minnesota defeat the Avalanche and Canucks (also a series comeback) before losing to the Anaheim Ducks in the Western Conference Semifinals.  Even though Minnesota’s 2003 Stanley Cup playoff run was very impressive as a whole, the series comeback and win against the Avalanche was especially commendable.

Players such as Milan Hejduk, Peter Forsberg, Joe Sakic, Adam Foote, Patrick Roy, and Alex Tanguay headlined the Avalanche lineup in the playoff series, but the Wild were somehow able to recover and pull out three straight victories with a lineup that had considerably less talent than the seasoned Colorado team for one of the most notable Stanley Cup upsets of all time.

Greatest Stanley Cup Upsets #2: 2010 Eastern Conference Semifinals

Philadelphia Flyers vs. Boston Bruins

The Philadelphia Flyers were the most recent NHL team to come back from a 3-0 series deficit when they beat the Boston Bruins in the 2010 Stanley Cup playoffs. Despite being in a hole, Philadelphia opted to trust Michael Leighton and the goalie rewarded the decision as he helped the team mount a historic comeback against the Bruins.

Aside from winning four straight games against Boston, the Flyers had to work for their win in a decisive Game 7 at the TD Garden. The seventh game started off horribly for the road team as Boston took a 3-0 lead just 14:10 into the first period and looked poised to take the series. However, Philadelphia slowly chipped away at the Bruins’ lead and Simon Gagne completed the comeback with a game-winning power-play goal during the late stages of the third period.

Sam Gagner
Sam Gagner, Philadelphia Flyers (Amy Irvin / The Hockey Writers)

What was ironic about the Bruins’ collapse was the fact that the team had suffered the same fate during the 1979 semifinals when Don Cherry’s team was called for too many men on the ice against the Montreal Canadiens. Even though the two series were played more than three decades apart, the Bruins were undone by the same penalty and it cost the team a chance to play for the Stanley Cup on a couple of occasions. Even though the Boston Bruins won the Stanley Cup in 2011, the team’s meltdown in 2010 was just another illustration of how unpredictable playoff hockey can be.

Greatest Stanley Cup Upsets #1: 1982 Divison Semifinals

Los Angeles Kings vs. Edmonton Oilers

This series had it all. Wild scoring, Wayne Gretzky, and a miraculous comeback on behalf of the Los Angeles Kings.

However, this series might just be remembered for the Miracle on Manchester as it was undoubtedly the biggest turning point of the series for both teams. The Edmonton Oilers came into the series boasting players such as Wayne Gretzky, Grant Fuhr, Jarri Kuri, Mark Messier, and Paul Coffey, but the Los Angeles Kings found a way to upset the powerhouse Oilers.

Marcel Dionne
Marcel Dionne, Los Angeles Kings, Nov. 14, 1984 (Photo by Graig Abel Collection/Getty Images)

Back in 1982, the Division Semifinals were a best of 5 game series and the Los Angeles Kings stole the momentum at a very crucial point of the series. With the teams splitting Games 1 and 2, the Oilers looked poised to take Game 3 as they led 5-0 going into the third period of play. The Oilers’ bench was laughing at the Kings, but Los Angeles refused to go away and steadily clawed away at Edmonton’s lead. With just under five minutes left in Game 3, the Kings had cut the deficit to 5-3 and headed to an extended power-play as Edmonton was assessed a five-minute major penalty for high sticking.

The Kings cashed in on their man-advantage and refused to give up even as Mario Lessard was pulled from his crease in favor of an extra attacker. With only five seconds left in regulation, the Kings tied the game and forced overtime. The death strike came very quickly for the Oilers as Daryl Evans scored the game-winning goal just over two minutes into the sudden death frame.

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The loss to the Kings was definitely a frustrating one for the Oilers, but it greatly shifted momentum in the series as the Kings were able to knock off Edmonton in Game 4. The odds were massively stacked against the Kings going into the series and the point differential between the two teams at the end of the regular season suggested that there was not even a sliver of hope for Los Angeles.

Even though the 1982 Los Angeles Kings lost to the Vancouver Canucks in the very next round of the playoffs, the Kings offered a great example of what happens when a team takes its foot off of the pedal during the Stanley Cup playoffs.

For those that were too young or have forgotten, here are some highlights from the Miracle on Manchester:

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Greatest Stanley Cup Upsets: Honorable Mentions

2003 Western Conference Quarterfinals: Anaheim Ducks vs. Detroit Red Wings

Many hockey fans did not expect to see what they saw in the first round of the Western Conference playoffs when the Red Wings and Ducks squared off.

The Red Wings were still very much a powerhouse in 2003, but J.S Giguere stood tall for the Ducks as they made an unexpected and thrilling ride to the Stanley Cup Finals. Even though the team was beaten by the Devils, the Ducks had to work hard to get to face the Devils. The Ducks swept the number-two seeded Wings out of the playoffs and proceeded to beat the Dallas Stars and Minnesota Wild en route to a Stanley Cup Finals appearance.

Paul Kariya, stanley cup upsets
Paul Kariya. (Brian Bahr/Getty Images/NHLI)

Fun Fact: The Ducks won every single game of the Detroit series by a one goal margin, with one of the most memorable wins being a triple OT game that Paul Kariya won after Giguere faced a barrage of 64 shots.

2010 Eastern Conference Quarterfinals: Montreal Canadiens vs. Washington Capitals

This quarterfinals matchup is one of the Stanley Cup upsets that could not be ignored. Jaroslav Halak put on an amazing shows during the 2010 Stanley Cup playoffs as the Canadiens ousted the Capitals after being down 3-1 in the series. The Canadiens went on to stun the Pittsburgh Penguins in the Conference Semifinals right after they dispatched the Capitals, and Halak was responsible for much of the success of the number-eight seeded 2009-10 Montreal Canadiens.

2021 Canadian Division Round 1: Toronto Maple Leafs vs. Montreal Canadiens

Down 3-1 heading into Game 5, against a universally-acknowledged better Maple Leafs team, with superstar weapons like Auston Matthews, Mitch Marner, John Tavares and William Nylander, the Canadiens rattled off three straight wins to take the series, and send the Maple Leafs and their long-suffering fans into another early offseason.

This article was originally published in April, 2012, and updated periodically.

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