Ranking the Biggest Playoff Upsets in NHL History

Rob VollmanContributor IApril 10, 2014

Ranking the Biggest Playoff Upsets in NHL History

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    Nick Ut

    1982's "Miracle on Manchester" between the Kings and the Oilers was just one of many shocking postseason upsets. In a seven-game series, even a heavy favorite will lose about one time out of every eight. What were history's most dramatic underdog victories?

    While it's difficult to use analytics to find history's greatest upsets, it does have some value. The basic approach is to look at the gap between the two teams in the regular-season standings and sort the upsets by those with the widest margins.

    From there, it must be determined if the team with the lesser record truly was a weaker team or was a good team that just had a poor stretch or some fluke injuries in the regular season. This can be done by looking at how many All-Stars and/or future Hall of Famers were on the team and how they did the season before and after.

    Adjustments can then be made for the different scoring eras and playoff formats, to mention only a few additional factors.

    In the end, it's never an exact science, and there's admittedly a fair deal of personal opinion. With those difficulties in mind, let's turn over to find out which series were the 10 biggest upsets in playoff history.

     

    All advanced statistics are via writer's own original research unless otherwise noted.

     

10. Edmonton Oilers Beat the Detroit Red Wings, 2006

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    PAUL SANCYA

    The Underdog

    The Edmonton Oilers snuck the final postseason spot away from the Vancouver Canucks, thanks to the NHL's new shootout rules.

    Securing a league-high 39 points by taking a league-high 26 games into overtime and shootout, the otherwise-.500 Oilers finished with 95 pointstheir most in 18 years, and their most since. The following season, they were tied for fifth-to-last in the NHL.

    This was mostly a team of hard-working role players. Other than superstar defenseman Chris Pronger, only four Oilers have ever played in an All-Star Game before or since, each of them only a single timeDwayne Roloson, Sergei Samsonov, Ryan Smyth and Shawn Horcoff.

     

    The Favorite

    Detroit was a truly dominant team in the regular season, winning the Presidents' Trophy with 124 points and a winning percentage of .756.

    The Red Wings had only 16 regulation-time losses, at least five fewer than any other team. They were second in both goals scored and fewest goals allowed. They also had only a single regulation-time loss in their final 20 games, which was on the last game.

    This was Detroit's sixth season in a 12-year run of 100-point seasons that was only ended by the lockout-shortened 2013 season. The Red Wings were in the middle of a three-year stretch when they earned a combined 346 points, far more than their opponents' 255.

    Detroit's lineup featured eight 20-goal scorers and four players with at least 80 points. It included four future Hall of Famers and five more players who have participated in All-Star Games either before or since, two of them multiple times.

     

    What Happened?

    Despite being outshot, 238-155, the Edmonton Oilers outscored the Red Wings, 19-17, in a six-game series. It was a first-round upset victory reminiscent of their surprise triumph over the Dallas Stars in 1997.

    Buoyed by trade-deadline acquisition Roloson and great defensive play, the Oilers went all the way to the Stanley Cup Final, losing to the Carolina Hurricanes in seven games.

9. Chicago Black Hawks Beat the Toronto Maple Leafs, 1938

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    Uncredited

    The Underdog

    The Chicago Black Hawks (as they were named until 1986) earned only 37 points in 48 games, keeping them only eight points out of last place in the eight-team NHL.

    As poor as that sounds, it was actually more points than they recorded in the prior or following seasons.

    Their two top players, Paul Thompson and Johnny Gottselig, were both in their 30s and past their prime. They only had two future Hall of Famers in Carl Voss and Earl Seibert, and the former was in his final season.

    The Black Hawks were by no means a disaster, but they were certainly one of the league's weakest teams at the time.

     

    The Favorite

    The Toronto Maple Leafs competed for the Stanley Cup eight times between 1932 and 1942, their only victories occurring in those first and last seasons.

    Despite that success, they weren't exactly a powerhouse, usually finishing the regular season only slightly above .500.

    In 1937-38, they finished with 57 points in 48 games, tops in the Canadian Division and third overall (out of eight teams). They had also swept the rock-solid Boston Bruins in three really close games to get to the Stanley Cup Final against Chicago.

    Toronto had five future Hall of Famers all essentially in their primes, including Gordie Drillon, Syl Apps, Busher Jackson, Red Horner and goalie Turk Broda.

     

    What Happened?

    Chicago, a team with a .385 winning percentage in the regular season, won the Stanley Cup. According to Frank Calder, the trophy had literally already been sent to Toronto before the series beganas reported in the Chicago Tribune—given the slim odds of a Black Hawks victory.

    The Black Hawks kept Toronto to a single goal in three of the four games, which is impressive given that injuries and various other controversies forced them to use three different goalies. Game 1 was backstopped by their opponent's minor league goalie, Alfie Moore, who was notified at the last minute while in the process of getting quite intoxicated. Games 3 and 4 were played by their regular goalie, Mike Karakas, who required a special skate to protect his foot.

    It was a great victory for American hockey. Bill Stewart became the first American-born coach to the win the Stanley Cup and the last one until Bob Johnson with Pittsburgh in 1991. This team was mostly American, an extremely rare and difficult feat at the time.

8. Florida Panthers Beat the Pittsburgh Penguins, 1996

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    Florida Panthers players celebrate their 3-1 victory over the Pittsburgh Penguins in game 7 of their Eastern Conference playoff series, in Pittsburgh, Saturday June 1, 1996. The Panthers will face the Colorado Avalanche in the Stanley Cup finals. (AP Phot
    GENE J. PUSKAR

    The Underdog

    The three-year-old Florida Panthers had reached the Eastern Conference Final in what would be their first of four playoff appearances in their 20-year franchise history.

    They had actually placed a strong seventh in the regular season with 92 points and had dispatched both the Boston Bruins and Philadelphia Flyers with limited difficulty.

    The lopsided nature of this series was based on Florida's lack of individual stars. There were no future Hall of Famers, and only two players would enjoy multiple All-Star Game appearancesveteran goalie John Vanbiesbrouck and 19-year-old rookie defenseman Ed Jovanovski. Their leading scorers were Dave Lowry, Ray Sheppard, Stu Barnes and Bill Lindsay. 

     

    The Favorite

    Despite being three seasons removed from their back-to-back Stanley Cup championships, the Pittsburgh Penguins were still a mighty team.

    Guided by Mario Lemieux, who won the Hart Trophy and led the league in goals (69), assists (92) and points (161), the Penguins finished fourth overall with 102 points, their 362 goals (including 109 on the power play) leading the league by 36.

    In addition to Hall of Famers Lemieux, Ron Francis and Jaromir Jagr (inevitably), the team also featured multi-time All-Stars Tomas Sandstrom, Glen Murray and Sergei Zubov.

    The Penguins were 10 points better than Florida this season and combined to be 10 points better over the prior and following seasons.

     

    What Happened?

    The Florida Panthers had a hot goalie and played a strong (and often boring) defensive system that ultimately prevailed in a gripping seven-game series.

    Ten years removed from his Vezina season, the 32-year-old Vanbiesbrouck posted a .932 save percentage throughout the postseason.

    As for the Penguins, their lack of secondary players left them reasonably beatable whenever their top lines could be shut down. That normally tall order was made slightly easier by Lemieux's serious flu.

    Florida would be swept in the Stanley Cup Final by the Colorado Avalanche.

7. Anaheim Mighty Ducks Beat the Detroit Red Wings, 2003

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    KEVORK DJANSEZIAN

    The Underdog

    Anaheim was making only its third postseason appearance in its 10-year franchise history and was facing the team that swept it the previous two times.

    The Mighty Ducks earned 95 points that season and finished more than three games over .500 for the first time in franchise history. They were not a high-powered offensive team, however, as 19-year-old rookie Stanislav Chistov finished the regular season as the team's fourth-leading goal scorer with just 12 goals.

    Other than 40-year-old future Hall of Famer Adam Oates, the Mighty Ducks had only three players who ever competed in an NHL All-Star Gamesuperstar Paul Kariya, defenseman Sandis Ozolinsh and goalie Jean-Sebastien Giguere.

     

    The Favorite

    The Detroit Red Wings were the defending Stanley Cup champions and were four seasons into their 12-season streak of 100-point seasons.

    Their 110 points were third-most in the NHL, giving them a 15-point edge over Anaheim that season and a 95-point advantage when combined with the prior and following seasons. The Red Wings led the league with 269 goals. They boasted three 30-goal scorers in a very low-scoring era. 

    The team was absolutely stacked with seven eventual Hall of Famers in Steve Yzerman, Brett Hull, Luc Robitaille, Brendan Shanahan, Igor Larionov, Chris Chelios and—inevitablyNicklas Lidstrom, along with five multi-time All-Star Game participants in Sergei Fedorov, Pavel Datsyuk, Henrik Zetterberg, Mathieu Schneider and goalie Curtis Joseph.

    The Red Wings finished the season white hot, losing only three of their final 27 games in regulation time. If they had a flaw, it was that the team was a little old. There were only four players in their 20s, and Detroit even had two in their 40s.

     

    What Happened?

    Anaheim became the first team to sweep the defending champions in the first round since Detroit did it to Toronto in 1952.

    Each of the four games was decided by a single goaltwo of them requiring overtime. Detroit outshot Anaheim, 171-120, but only got six goals past eventual Conn Smythe winner Giguere.

    The Mighty Ducks would advance to beat Dallas in six games before sweeping Minnesotaa team that pulled off a stunning opening-round upset of its own over Coloradoin the Western Conference Final. The Cinderella story didn't end until seven games later when the New Jersey Devils shut them out for the third time in a series to win the Stanley Cup.

    This kicked off a new tradition of postseason success. Anaheim would win the Stanley Cup four years later after being rebranded as the Ducks and upset the Presidents' Trophy-winning San Jose Sharks in the first round two years after that.

6. Minnesota North Stars Beat the Chicago Blackhawks, 1991

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    Fred Jewell

    The Underdog

    Minnesota finished with 68 points in Bob Gainey's first season as coach, only good enough to rank 16th out of 21 teams. The team dropped five of its last six games.

    Minnesota hadn't finished above .500 in five years and would manage it only once in the following five years. It hadn't won a playoff series in five years, either.

    The team was without any future Hall of Famers, although it had nine players who competed in at least one All-Star Game during their careers, most notably Bobby Smith, Mike Modano, Brian Propp and Brian Bellows.

     

    The Favorite

    Chicago won the Presidents' Trophy with 106 points, a 38-point advantage over its first-round opponent.

    Rookie goalie Ed Belfour won the Vezina while Dirk Graham won the Selke as the league's best defensive forward, joining a select club with teammate Troy Murray.

    Though Belfour and Chris Chelios are the only two players on that team currently in the Hall of Fame, Dominik Hasek and Jeremy Roenick will likely someday follow. Dave Manson, Doug Wilson and Steve Larmer were also multi-time All-Star Game participants.

     

    What Happened?

    For the first time in 20 seasons and only the second time in the post-1967 expansion era, the Presidents' Trophy winner was eliminated in the first round.

    What's particularly surprising is that it wasn't a squeaker, but rather a decisive victory. The North Stars won the first game, 4-3, in overtime before dropping the next two by a combined score of 11-7. However, they dominated the rest of the way. Minnesota won the last three games by a combined score of 12-2 and outshot Chicago, 222-159. 

    Chicago's weakness was discipline, combining for 274 penalty minutes in that single series. Minnesota consequently scored 15 power-play goals in the series, tying an NHL record.

    Minnesota continued its unlikely postseason run past the St. Louis Blues in six games and the defending Stanley Cup champion Edmonton Oilers in five before falling to the Pittsburgh Penguins in the Stanley Cup Final in six games.

    Chicago would reach the Stanley Cup Final the next season and matched their 106 points the season after that.

5. Montreal Canadiens Beat the Washington Capitals, 2010

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    Nick Wass

    The Underdog

    Montreal's 88 points were four below the league average and was its worst total since 2003.

    The Canadiens were above average defensively but had real difficulty scoring. They finished tied for 23rd with just 217 goals scored, over 100 fewer than their first-round opponent.

    Brian Gionta, with just 28 goals and 46 points, was the team's leading goal scorer and finished fourth in team scoring. The Habs had only two other 20-goal scorers, less than half as many as the Capitals.

    Montreal ended the season on a three-game losing skid and dropped eight of its last 11.

     

    The Favorite

    Washington won the Presidents' Trophy with 121 points, 33 more than its first-round opponent and the most in franchise history.

    The Capitals were at their peak, as they were in the middle of a three-year period when they amassed a combined 336 pointsfar more than Montreal's 277. They would, however, extend their streak of Conference Final absences, which today stands at 15 seasons.

    Washington boasted two 100-point scorers in Alexander Ovechkin and Nicklas Backstrom. The team also had two 40-goal scorers in Ovechkin and Alexander Semin, and it had five other 20-goal scorers. Mike Green scored 76 points on the blue line and was one goal shy of scoring 20 himself.

    Washington finished its season winning five of its last six.

     

    What Happened?

    The first two games in Washington went to overtime, with each team winning one. Washington then dominated the Canadiens by a combined score of 11-4 over the next two games in Montreal to go up three games to one.

    That's when things went badly for the Capitals. Montreal goalie Jaroslav Halak slammed the door shut, and the Caps managed only three goals the rest of the series. Despite outshooting Montreal, 134-65, the Capitals would lose three straight games

    The Canadiens went on to upset the Penguins in seven games before falling to the Philadelphia Flyersanother team that finished with 88 pointsfour games to one in the Eastern Conference Final.

    Given how some analysts used analytics to correctly predict this upset, most famously Olivier Bouchard of Behind the Net, I was hesitant to include it in this list. The Kings' 2012 Stanley Cup run also falls into similar territory. If you were into analytics at the time, feel free to substitute Montreal's first-round upsets over the Boston Bruins in either 2002 or 2004 instead.

4. Toronto Maple Leafs Beat the Montreal Canadiens, 1945

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    Noah Graham/Getty Images

    The Underdog

    The Toronto Maple Leafs were a remarkably average team. They finished two games over .500 after being exactly .500 the year before and would post a .450 winning percentage the following year. They had won just five of their last 14 games.

    The Maple Leafs had three future Hall of Famers in their lineup, including Babe Pratt, a 19-year-old Ted Kennedy and a near-retirement Sweeney Schriner.

     

    The Favorite

    Montreal lost only eight games all season and only five games the season before. It won the Stanley Cup in 1944 and would again in 1946. It was the best team in hockey by some margin.

    This was the season when Maurice Richard became the first player to score 50 goals in 50 games. His center, Elmer Lach, won the Hart Trophy after winning the scoring title and setting the new NHL record for assists with 54. Goalie Bill Durnan won the Vezina.

    The Canadiens boasted three more future Hall of Famers in Toe Blake, Buddy O'Connor and Butch Bouchard.

     

    What Happened?

    Toronto eliminated Montreal in six games despite being outscored, 21-15. All four Maple Leaf victories were by a single goal while the Canadiens beat Toronto by scores of 4-1 and 10-3.

    The Maple Leafs would go on to beat the Detroit Red Wings in the seven-game final, hoisting their fifth Stanley Cup in team history and their first since they upset the highly favored Red Wings in 1942.

    They would miss the playoffs the subsequent season but would win the Stanley Cup four more times in the following five years.

3. San Jose Sharks Beat the Detroit Red Wings, 1994

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    Lennox McLendon

    The Underdog

    It was San Jose's third NHL season and its first playoff appearance. The Sharks earned just 63 points in 164 games over their first two seasons, and in 1993-94, their 82 points in 84 games was 17th out of 26 teams.

    The team was built around Russians and Latvians. Igor Larianov, Sergei Makarov, Johan Garpenlov and Sandis Ozolinsh were all top-five postseason scorers for the team, and Arturs Irbe was the goalie.

    The Sharks were without any true superstars. Larionov was the only future Hall of Famer, and Ozolinsh's seven All-Star Game appearances were two more than the rest of the team combined.

     

    The Favorite

    Coached by the great Scotty Bowman for the first time, Detroit was four seasons into its current streak of 23 straight postseason appearances.

    The Red Wings finished the regular season with 100 points for the second consecutive season, which was good for fourth-best overall. Their 273 combined points over this season and the prior and following seasons would almost double San Jose's 146.

    The team boasted four current Hall of Famers (Steve Yzerman, Mark Howe, Paul Coffey and Dino Cicarelli), two who will no doubt be named soon (Nicklas Lidstrom and Sergei Fedorov), two multi-time All-Stars (Chris Osgood and Keith Primeau) and four more players of distinction (Bob Probert, Vladimir Konstantinov, Kris Draper and Steve Chiasson). In short, it was stacked.

     

    What Happened?

    Detroit got out to a 2-1 series lead, outscoring San Jose, 11-7, in the first three games. The Sharks won the next two at home before suffering a 7-1 beatdown when the series went back to Detroit. San Jose pulled off the upset with a 3-2 win in Game 7, thanks to a third-period game winner from Jamie Baker.

    In the following round, the Sharks were eliminated by the Maple Leafs in seven games.

    Though the Sharks beat the Red Wings despite being outscored, 27-21, they would face the Red Wings again the following year after upsetting the highly favored Flames in a first-round series where they were outscored, 35-26. This time, Detroit would eliminate San Jose in a four-game sweep that was dubbed the tennis seriesthe scores were 6-0, 6-2, 6-2 and 6-2.

    Another notable upset in San Jose history occurred five years later when the Sharks upset the Presidents' Trophy-winning St. Louis Blues despite a 27-point gap in the standings.

2. New York Islanders Beat the Pittsburgh Penguins, 1993

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    Alex Brandon

    The Underdog

    The Islanders were not a strong team. They finished just three games above .500 and were without their superstar, Pierre Turgeon, who had been injured in one of hockey's worst cheap shots after celebrating a little too earnestly in a blowout victory over the Capitals in Round 1.

    The Islanders only had three players who would ever appear in an All-Star Game, with Uwe Krupp, Brian Mullen and Ray Ferraro each playing exactly once.

    The team had missed the postseason the previous two years and three of the last four. They would scrape into the postseason once more the following season before a seven-year absence.

     

    The Favorite

    The Pittsburgh Penguins had won the Presidents' Trophy with 199 points, their best season in franchise history before or since. They were looking for their third consecutive Stanley Cup, a potential dynasty in the making.

    Mario Lemieux was the greatest player on the planet, winning the Hart Trophy and the scoring race in just 60 games. His fellow future Hall of Famers included Ron Francis, Joey Mullen, Larry Murphy and Jaromir Jagr (soon enough) while the team also featured multi-time All-Stars Mike Ramsey, Rick Tocchet and Kevin Stevens.

    The Penguins had a 32-point edge over the Islanders in the regular season and a combined 25-point edge in the prior and following seasons.

     

    What Happened?

    David Volek scored the Game 7 overtime winner to end Pittsburgh's potential dynasty. It was a game where the Islanders were outshot, 45-20, including 20-7 in the first period.

    Penguins goalie Tom Barrasso struggled in net while Islanders 20-year-old rookie defenseman Darius Kasparaitis knocked Lemieux off his game in a way that wasn't felt to be possible.

    It was also an upset reminiscent of the 1975 matchup between these two teams when the Islanders erased a 3-0 series deficit to knock off the Penguins.

    The Islanders were eliminated by the Montreal Canadiens four games to one in the following round, and the Penguins wouldn't reach the Stanley Cup Final again for another 15 years.

1. Los Angeles Kings Beat the Edmonton Oilers, 1982

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    The Underdog

    The Los Angeles Kings were coming off a strong 99-point season but were otherwise in an 11-year stretch where they had only two other seasons above .500.

    In 1981-82, their 63 regular-season points ranked 17th out of 21 teams, and they changed coaches midseason from Parker MacDonald to Don Perry. The Kings had won just two of their preceding 14 postseason contests over the past four seasons.

    They did have the famous Triple Crown Line of Marcel Dionne, Dave Taylor and Charlie Simmer, along with some future Hall of Famers in Larry Murphy and Bernie Nicholls (some day).

     

    The Favorite

    The Edmonton Oilers were the second-best team in hockey, scoring a then-record 417 goals on their way to 111 points.

    They were coming off a season where they pulled off a dramatic first-round upset of their own over the Montreal Canadiens in 1980-81.

    The Oilers were absolutely stacked with future Hall of Famers, including Wayne Gretzky, Mark Messier, Paul Coffey, Jari Kurri, Grant Fuhr and Glenn Anderson, not to mention multi-time All-Stars Garry Unger and Kevin Lowe. 

    In the regular season, the Oilers outscored the Kings, 51-27, including two victories by 11-4 and 10-3 margins.

     

    What Happened?

    One of hockey history's greatest single-game comebacks, dubbed the "Miracle on Manchester," occurred late in Game 3. The five-game series was tied at one game apiece, but the Oilers were up 5-0 at the end of the second period. The Kings would win the game, 6-5, in overtime.

    After dropping Game 4, the Kings would complete the upset with a 7-4 victory in Edmonton in Game 5. The star of both that game and the series was surprisingly 21-year-old rookie Daryl Evans, whose NHL career would only last 113 games.

    The Oilers were the most potent offensive team to date, but they were also a young team prone to arrogance and mistakes, and their open style of hockey created a lot of chances for both teams. The Kings capitalized on a higher portion of theirs.  

    The Kings would be eliminated by Vancouver, four games to one, in the following round while the Oilers would make the Stanley Cup Final in six of the following eight seasons, winning it five times.

     

    Rob Vollman is author of Rob Vollman's Hockey Abstract, co-author of the annual Hockey Prospectus guides and a featured ESPN Insider writer. @robvollmanNHL.