Top 15 Biggest Choke Jobs in Stanley Cup Playoff History

The history of the NHL playoffs is filled with upsets and almost every year there is at least one series in the first round that you could deem an upset. So far this year the Blackhawks losing to the Blues could be considered a mild upset as well as the case that the Sharks and Islanders beat the Kings and the Panthers respectively, could also be considered upsets. This article will focus on the biggest upsets I could dig up and most of them either involve an eight seed beating a number one seed or a seventh seed defeating a number two seed. As well, in most cases the team that won did not progress very far in the playoffs and the upset occurred in the first round of the Stanley Cup Playoffs.

The teams that were upset are also some of the most successful teams in modern NHL history. From the Detroit Red Wings to the Pittsburgh Penguins, this article will show that even the best teams can lose in the NHL in a seven game series. As far as the list is concerned, I tried to put the team that won with the fewest All-Star calibre players at the top of the list and those with elite talent closer to the bottom

Researching for this article made me recollect playoffs of the past and reminded me that in pro sports anyone can win. It is a little bit harder in hockey I believe since it is a seven game series and usually the team with more talent comes out on top, but this list will prove that’s not always the case. Sometimes things such as team chemistry and a really hot goalie are enough to ride a team through the playoffs and there have been plenty of teams in the past that have won Stanley Cups with this logic.

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15 Pittsburgh Penguins - 1996

via sportsnet.ca

The Penguins were led by Mario Lemieux who led the year in points, goals and assists on his way to the Hart and Art Ross Trophy. They also had All-Stars Tomas Sandstrom, Sergei Zubov and Glen Murray along with current Hall of Famer Ron Francis and future Hall of Famer Jaromir Jagr. The Panthers were lead by their goalie John Vanbiesbrouck who posted a .932 save percentage throughout the postseason but was 10 years removed from his only Vezina Trophy win. The rest of their roster was led by a rookie defenceman and the likes of Stu Barnes, Ray Sheppard and Dave Lowry who were role players throughout their careers.

This did not matter and Vanbiesbrouck remained hot and the Panthers beat the Penguins in the 1996 Eastern Conference Final but ultimately lost to the Colorado Avalanche in the Stanley Cup Final in a four game sweep.

14 Bruins Blow Two 3-0 Leads - 2010

via newyork.cbslocal.com

This second round series might be more upsetting than an upset since it was only the third time in NHL history, and first time since 1975 that a team came back from being down 3-0 in a series to win. Not only did the Flyers complete the unlikely comeback, they also overcame a 3-0 deficit in the series deciding seventh game. The Flyers were led by little known goalie Michael Leighton who was their backup and he actually led them to the Stanley Cup Final which the Flyers lost to the Chicago Blackhawks in seven games.

13 Same old Leafs - 2013

via thestar.com

Another playoff series on the list that is more upsetting than an upset perhaps and doubly so since I am a die-hard Leafs fan. This series was a total roller coaster and when the Bruins took a 3-1 series lead in this first round matchup I thought it was over. However, in typical Maple Leafs fashion, the team stormed back to tie the series only to lose in historically miserable fashion in Game 7.

The Leafs took a 4-1 lead with ten minutes remaining and against all odds the Bruins won the game in overtime. This is by far the toughest thing I have had to deal with being a Leafs fan for over 30 years and this defeat alone should allow us suffering Leafs fans to better things in the future.

12 Stars fall to pesky Oilers - 1997

via theoldreader.com

Here we have a now iconic first round matchup featured the seventh seeded Edmonton Oilers and the second seeded Dallas Stars. The Oilers were led by a hot Curtis Joseph and the Stars had future Hall of Famers Mike Modano and Joe Nieuwendyk along with players like Pat Verbeek and Sergei Zubov. This did not matter as the Oilers were able to ride Joseph to a tough seven game series win in which three of the Oilers' four wins came in overtime and CuJo picked up two shutouts, before losing to the Colorado Avalanche in the second round.

11 Penguins Dynasty Ends - 1993

via newsday.com

The Islanders won in the first round of the 1993 NHL playoffs in a mild upset, but what they did in the second round was an upset of epic proportions. Without their superstar Pierre Turgeon who suffered a cheap shot at the hands of Dale Hunter in the first round, the Islanders really did not stand any chance at all on paper to defeat the heavily favored Penguins.

Once again led by Mario Lemieux, the Penguins had won two cups in a row and were looking to build a dynasty. However, David Volek ruined all of their dreams in Game 7 with an overtime winner.

10 Kings Over Red Wings - 2001

via theroyalhalf.com

Another upset involving a seven and number two seed, the powerhouse Red Wings had 111 points during the regular season compared to just 92 points from the Kings, but none of that mattered in this hard fought six game series. The Red Wings dominated the Kings in the first two games, winning 5-3 and 4-0, but the Kings won the next four games, including two in overtime. They even overcame a three goal deficit in Game 4. They would eventually win the series with a clinching goal came by Adam Deadmarsh in the extra frame of Game 6.

9 Leafs Over Sens - 2001

via ottawacitizen.com

The second instalment in the Battle of Ontario between the seventh seeded Leafs and the second seeded Senators wound up being more like a walk in the park for the Toronto Maple Leafs. Led by an inspired performance by goalie Curtis Joseph the Leafs were able to sweep the 109-point regular season Ottawa Senators - who had swept the regular season series - in four straight games. Joseph’s game was so on point during this series that the Senators did not score their first goal until final four minutes of Game 3. This was a pattern for the Sens of the early 2000s, who would always come up short when it mattered most.

8 Ducks Over Red Wings - 2003

via thehockeywriters.com

The Ducks only had future Hall of Famer Adam Oates who was 40 years old and at the end of his days along with Paul Kariya, Sandis Ozolinsh and J-S Giguere who had ever played in an All-Star game while the Red Wings were blessed with four 30 goal scorers in a very low scoring era. They were also stacked with seven future Hall of Famers along with five multi-time All-Star game participants. None of this mattered and the Ducks rode Giguere to a series sweep and all the way to the Stanley Cup Final which they lost to the New Jersey Devils in a seven game series. Giguere however was one of only five winners of the Conn Smythe Trophy as a member of the losing team. The Ducks would win a Stanley Cup four years later.

This was a Red Wings team expected to defend their Stanley Cup championship, so to go out in four straight was an incredible disappointment.

7 Oilers Blow Lead and Series - 1982

via thescore.com

The third game of this series is known as the “Miracle On Manchester” for the amazing comeback that the Kings pulled off in Game 3. The Kings were down 5-0 at the end of the second period, but the Kings wound up winning the game 6-5 in overtime. That victory put the Kings ahead 2-1 in the series and they wound up defeating a heavily favored Oilers team that featured some of the best players in NHL history in five games. This series is not higher on my list because the Oilers were just in their first year of building a dynasty and were prone to mistakes and the Kings had the infamous Triple Crown Line which is one of the best lines in NHL history.

6 Red Wings Throw Away Historical Season - 2006

via oilersnation.com

The Oilers were a group of hard working players even though they did have Chris Pronger on the blue-line. They had a couple of former NHL all-stars such as Sergei Samsonov and Ryan Smyth, but they were nothing compared to what the talent laden Red Wings could bolster. During the 2005-06 regular season the Wings had one of the most dominant seasons in NHL history and won the Presidents' Trophy with 124 points and had only a single regulation loss in their final 20 games.

The Wings lineup included four future Hall of Famers and four players with at least 80 points. The Oilers were outshot 238-155 but won this series in six games and outscored the Red Wings 19-17. Led by trade deadline acquisition Dwayne Roloson the Oilers rode his hot play all the way to the Stanley Cup Final, losing to the Hurricanes in seven games.

5 Same old Sharks - 2009

via thehockeywriters.com

The San Jose Sharks are known for playoff failure in recent memory and this loss to the eighth seeded Ducks was perhaps their biggest. The Sharks were coming off a Presidents' Trophy win during the regular season and were expected to roll throughout the playoffs. Unfortunately, they ran into a hot Jonas Hiller and a team led by NHL superstars Corey Perry and Ryan Getzlaf and Hall of Famer Scott Niedermayer. They were shutout twice by Hiller during the series and lost this first round match in six games.

4 Devils Underestimate Sens - 1998

via thescore.com

The Devils finished the regular season atop the Eastern Conference standings with 108 points and the Senators were the eighth seed with just 83 points and entered the playoffs with very low expectations. The series was supposed to be an easy win for the Devils and when the Devils' Randy McKay was asked ahead of the series who he respected on the Senators, he replied, "To be honest, I'd have to see their (roster) list." The Senators were led by the likes of Alexei Yashin and Daniel Alfredsson who led the team with a hat trick in Game 4 to give them an insurmountable 3-1 series lead. The Senators would complete the major upset in six games.

3 History Beats Talent - 2010

via hockeyinsideout.com

The one thing missing from Ovechkin’s mantle is a Stanley Cup and 2010 might have been his best chance not including this season. The 2009-10 Washington Capitals won the Presidents' Trophy and boasted two 100-point scorers, Ovechkin and his partner in crime Nicklas Backstrom. The team also has two 40-goal scorers in Ovechkin and Alexander Semin and five other 20-goal scorers.

Conversely the Habs' leading point scorer was Brian Gionta who only managed 46 points, but the team had Jaroslav Halak who slammed the door shut on the mighty Capitals and led his team to victory to in seven games, with the Capitals blowing a 3-1 series lead.

To date, it's the only first seed to blow a 3-1 series lead to an eighth seed. Looks like the Habs' history of winning trumped Washington's talent, whose history is full of shortcomings.

2 St. Louis sings the Blues - 2000

via orlandosentinel.com

The 1999-00 St. Louis Blues were led by Hart Trophy winner Chris Pronger and Hall of Famer Al MacInnis on defence and 500-goal scorer Pierre Turgeon up front. They won the President’s Trophy during the year and it was one of the best in the franchises history. However, in the first round of the playoffs they had trouble with the Sharks who were led by captain Owen Nolan and defeated the mighty Blues in seven games.

This series is as high as it is on my list because unlike most of the upsets I mentioned the Sharks did not have a goalie steal any games and it was more of a team effort that led them to victory.

1 Wings Dynasty Put on Hold - 1994

via bleacherreport.com

The 1993-94 San Jose Sharks only had one NHL All-Star and that was largely because in this era every team had to have one representative. The 1993-94 Red Wings. like their other teams mentioned in this article were blessed with current and future Hall of Famers as well as multiple all-star game participants. The Sharks wound up winning the series in seven games but would lose to the Maple Leafs in the next round also in seven games. This is number one on my list because of the lack of star power on the Sharks. The Red Wings should have marched right to the Finals for a showdown with the Rangers.

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