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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.

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.

14 Bruins Blow Two 3-0 Leads - 2010

via newyork.cbslocal.com

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.

12 Stars fall to pesky Oilers - 1997

via theoldreader.com

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.

10 Kings Over Red Wings - 2001

via theroyalhalf.com

9 Leafs Over Sens - 2001

via ottawacitizen.com

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.

7 Oilers Blow Lead and Series - 1982

via thescore.com

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.

5 Same old Sharks - 2009

via thehockeywriters.com

4 Devils Underestimate Sens - 1998

via thescore.com

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.

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.

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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Top 15 Biggest Choke Jobs in Stanley Cup Playoff History