NHL Playoffs: The 10 Biggest Upsets in NHL Playoff History

Dave Ungar@@DaveUngar68Correspondent IIIApril 20, 2012

NHL Playoffs: The 10 Biggest Upsets in NHL Playoff History

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    The NHL playoffs.

    Each year, hockey's elite take to the ice for roughly two months to decide the issue of who is the best team in the world.

    The NHL playoffs is one of the most grueling, demanding and exciting tournaments in all of sports. "History will be made" is more than just a catchy advertising slogan—it is also the truth.

    Quite often, the history to be made comes in the form of a titanic upset. Next to March Madness, the NHL playoffs seem to produce the most frequent, and sometimes most stunning, upsets of any of the major sports out there.

    Why this seems to be the case is anyone's guess.

    Maybe it is because home ice advantage means very little in the playoffs, a sharp contrast to the NFL, MLB or NBA playoffs.

    Perhaps it has something to do with the gap in talent between a No. 8 seed and a No. 1 seed not truly being as great as in other sports.

    Perhaps it is something else entirely.

    Whatever "it" is, the fact remains that the history of the NHL playoffs is rich in shocking moments and mind-bending upsets.

    With so many upsets having taken place, what are the 10 biggest upsets in the history of the NHL playoffs?

    Let's find out.

What Is an Upset?

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    Anyone who has been a hockey fan for any length of time is very familiar with the video in this slide.

    On February 22, 1980, the US Olympic Hockey Team did not just pull off an upset when they beat the USSR—they delivered a miracle.

    In the NHL playoffs, however, there are no real miracles. But there are plenty of upsets.

    So, what is an "upset" for purposes of this article?

    Obviously, seeding has to be considered as a major factor. Whenever a No. 8 seed beats a No. 1, or a No. 7 beats a No. 2, that is going to automatically qualify as an upset. So seeding is a key consideration, but it is not the only one.

    Another factor I looked at was the lasting impact of an upset. In other words, was a dynasty or potential dynasty ended because of the upset? In many respects, an upset at one phase of the playoffs has a ripple effect throughout the rest of the tournament.

    Still another factor to consider is whether a stunning comeback took place. Some of the most lasting memories of the NHL playoffs are when teams have rallied back from a 3-1 deficit—or worse.

    You also have to consider the era in which an upset occurs. As you peruse this list, you will see more than a few upsets that took place during time frames before many of us were even born. Things were different back in the days of the Original Six, when all but two teams made the playoffs.

    There are also upsets that took place back in the days when some of the playoff series were best-of-five affairs, and not the current best of seven format. Would the outcome have been the same in a best-of-seven series? No one will ever know. But, for a five-game series, the result was shocking.

    Those are just some of the factors I looked at in researching this and compiling a list of the 10 biggest upsets in NHL playoff history.

    But, before we get to the top 10, let's look at some of the upsets that barely missed the cut.

Honorable Mentions

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    In putting together this collection of upsets, I came across four upsets that were certainly stunning, but for one reason or another, not quite stunning enough to get it into the top 10.

    Here, then, are the honorable mentions:

    1975 Quarterfinals: New York Islanders rally from 3-0 down to defeat the Pittsburgh Penguins

    The '75 Islanders were a relatively new franchise and had only been in existence for three years when this shocker took place. Islanders fans who know their history know that Billy Smith is the reason the Isles won four straight Stanley Cups from 1980 to 1983.

    In 1975, however, Smith was the reason the Islanders found themselves in a 3-0 hole. Enter Glenn "Chico" Resch, who gave up only four goals as the Islanders became only the second team (at that time) to come back from a 3-0 deficit to win a playoff series.

    1986 Smythe Division Final: Calgary Flames Dethrone a Dynasty

    The Edmonton Oilers were a dynasty in the making in the spring of 1986. They had won the previous two Stanley Cups and were favored to win a third consecutive title. But, in Game 7 of the Smythe Division Finals, the Oilers dynasty was interrupted, at least for a season, by the Calgary Flames, a very good team in their own right.

    For those who recall, Game 7 is infamous for the play where Oilers defenseman Steve Smith tried to clear the puck and inadvertently put it off of Grant Fuhr's leg and into his own net (see the video for this slide). That mistake would cost the Oilers the series—and it all happened on Smith's birthday no less.

    This one might have made the top 10 if the Flames had not been such a good team that year. When you beat a team with Wayne Gretzky, Mark Messier, Jari Kurri and Grant Fuhr, though, you at least deserve an honorable mention.

    2003 Western Conference Quarterfinals: The Mighty Ducks Sweep the Red Wings

    Back when the Ducks were still Mighty, they were a No. 7 seed, with an untested goalie, taking on the No. 2 seeded Red Wings. The Red Wings had won their division with 110 points and were considered a strong contender to win the Cup.

    Instead, they were swept by the Mighty Ducks, who rode the performance of Jean-Sebastian Giguere past the shocked Wings and all the way to Game 7 of the Stanley Cup Finals against the Devils. The Ducks would fall short in Game 7, but that magical run to the Final began with the sweep of the Red Wings, with the Ducks winning each game by only one goal.

    2009 Western Conference Quarterfinals: The Ducks Shock the Sharks

    Much to the chagrin of their fans, the San Jose Sharks have made a habit of folding in the playoffs. Their collapse in 2009 to the No. 8-seeded Ducks (who were no longer Mighty—but still very good) must be especially painful to them.

    Picked by many to finally get over the hump in 2009, the Sharks ran into a hot goalie in Jonas Hiller, could not handle Corey Perry or Ryan Getzlaf and were eliminated in just six games by the Ducks.

    Four classic upsets that are all noteworthy, but not quite epic enough to make the top 10.

    So, let's unveil the stunners that did make the list.

10. 1994 Western Conference Quarterfinals: San Jose Sharks Beat Detroit Red Wings

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    It was not always about playoff choke jobs for the San Jose Sharks.

    In 1994, in only their third year in existence, the Sharks stunned the highest scoring team in the NHL, the Detroit Red Wings, in a shocking seven-game upset.

    Arturs Irbe was the hero of this series as his spectacular play in goal allowed the Sharks to pull off this stunner.

    What made this so shocking was that the Sharks had finished a ghastly 11-71-2 the prior season. But, in 1993-1994, they qualified for the playoffs with 82 points, a record 58-point jump from the previous season.

    In Game 7, in Detroit, the Sharks would prove that they were about ready to move up in the NHL pecking order. Jamie Baker's goal proved to be decisive in the Sharks' upset win.

    The 1993-1994 Sharks were a better team, however, than many realize, and the gap between them and the Red Wings was only 18 points. That sounds like a lot, but not nearly as wide a gap as we will see later on. That is probably a key reason I have this upset at No. 10 and not higher.

    Regardless, they were certainly better than the Red Wings, or the rest of the hockey world, thought they were.

9. 1942 Stanley Cup Finals: The Leafs Rally from 3-0 Down to Beat the Red Wings

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    From a seeding standpoint, this is not an upset at all as the 1942 Toronto Maple Leafs were the favorites to win the Stanley Cup.

    What no one expected, however, was for the Leafs to be staring a 3-0 deficit in the face against the Detroit Red Wings.

    But the Leafs would win Game 4 on the road, crushed the Wings in Game 5 and then shut them out in Detroit in Game 6.

    The Leafs would then return to Toronto and cap the greatest comeback in NHL playoff history.

    Now, some may be wondering why this upset comes in at No. 9, but the 1975 Islanders, who pulled off a similar comeback, only got an honorable mention.

    The reason is that this is the only time a comeback of this magnitude has happened in the Stanley Cup Finals. In fact, this is the only time such a comeback has occurred with a world championship at stake.

    With the championship on the line, the Maple Leafs staged the most remarkable comeback possible, and that is why this upset comes in at No. 9.

8. 1993 Division Finals: New York Islanders End the Penguins Dynasty

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    A second Islanders victory over the Penguins, but this one does make the list.

    In 1993, the Penguins had won the past two Stanley Cups and seemed a lock to win a third straight championship. This is the Penguins team that had Mario Lemieux, Ron Francis and Jaromir Jagr, all pretty much in their prime. The Penguins had entered the playoffs on a 17-game win streak and had all the momentum in the world.

    The Islanders were far from a bad team, entering the playoffs as the No. 3 seed. They defeated the Washington Capitals in the opening round—the infamous series in which current Caps coach Dale Hunter clobbered Pierre Turgeon from behind, separating his shoulder. Turgeon, generally considered the Isles best player in 1993, missed the series against the Penguins.

    Though the Islanders were missing a key player, they played an extremely smart series against the Pens. By physically throwing Lemieux off his game, the Islanders slowed the Penguins enough to make a series out of it.

    In Game 7 (as seen in the video), David Volek would score in overtime as the Islanders shocked the Penguins and brought a premature end to their dynasty.

    Unfortunately for Islanders fans, the Isles have not won a playoff series since the No. 8 upset on this list.

7. 1938 Stanley Cup Finals: The Sub .500 Blackhawks Win the Cup

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    Record-wise, the 1937-38 Chicago Blackhawks were, well, not good.

    This is back in the days when the NHL season was only 48 games in length. Even so, the Blackhawks still posted a record of only 14-25-9, for a whopping total of 37 points. They finished a full 30 points behind the American Division-winning Bruins.

    But these were also the days when only the last place team in each division missed out on the playoffs, and luckily for Chicago, Detroit was two points worse.

    None of that mattered at all once the playoffs began, though, as the 'Hawks upset the Canadiens and then the New York Americans on the way to the finals against the Maple Leafs.

    The Maple Leafs had finished 20 points better than the Blackhawks during the regular season. This particular finals was notable for a few key events. Initially, the Blackhawks lost their starting goalie, Mike Karakas, to a toe injury and they actually had to call up a minor league goalie, Alfie Moore, for Game 1.

    Moore shut down the Leafs 3-1, but was then replaced. By Game 3, Karakas was back in net (with a steel toe guard in his skates, no less). Karakas would win the next two games, and the Blackhawks won the Stanley Cup in four games.

    In a low water mark for the NHL, however, the Blackhawks were unable to hoist the cup the night they won it. Frank Calder, the first president of the NHL, gave the Blackhawks no chance and actually had the cup sent to Toronto. So, it was not in Chicago the night the Blackhawks prevailed.


    The 1937-38 Blackhawks, a sub-.500 team that won the Stanley Cup, come in at No. 7 on this list.

6. 1945 Conference Semifinals: Toronto Shocks an Awesome Montreal Team

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    The 1944-45 Montreal Canadiens were one of the best teams ever—in the regular season, anyway.

    In a 50-game season, the defending champion Habs finished an amazing 38-8-4. That is a winning percentage of .800.

    By contrast, the Toronto Maple Leafs finished with a rather pedestrian mark of 24-22-4.

    The Canadiens finished 28 points ahead of the Leafs at season's end, so no one gave Toronto much chance at all when the two teams met in the conference semifinals.

    But that is why they play the games, and this was another example from the NHL's earlier years of how regular season success means very little once the playoffs start.

    Behind the excellent goaltending of Frank McCool, the Leafs would win the first two games, drop the third, win the fourth and then lose Game 5. Determined not to let the series go back to Montreal, the Maple Leafs completed the shocking upset with a 4-3 win in Game 6.

    The Maple Leafs won all four games by one goal.

    Not satisfied with one upset, the Maple Leafs would go on to beat the Detroit Red Wings, also heavily favored, in the Stanley Cup Finals in a classic seven-game series that saw the Wings rally from a 3-0 deficit—but fail to complete the amazing comeback.

    The over-achieving 1944-45 Maple Leafs check in with the sixth biggest upset in NHL playoff history.

5. 2010 Eastern Conference Quarterfinals: The Canadiens Rally to Beat the Caps

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    As a Caps fan, it still hurts to remember this colossal upset.

    It hurts even more to write about it as the fifth biggest upset in NHL playoff history.

    The 2009-2010 Capitals had one of the most potent offenses in recent NHL history. Their offense was so deadly that they rarely focused on defense and had no true defensive scheme to speak of. The Caps racked up 121 points as they skated to their first-ever President's Trophy.

    The Canadiens, on the other hand, barely even qualified for the playoffs with all of 88 points. No one gave the Habs much of a chance against Washington.

    But Montreal would stun Washington in Game 1 and were in firm control of Game 2 until a massive comeback by the Caps evened the series.

    When the Caps took both games in Montreal, and returned home with a 3-1 series lead, it was a foregone conclusion that the Caps would close things out, on home ice, in Game 5.

    It never happened. A big reason was that the Caps had the best power play in the NHL in 2009-2010, but they went a dismal one-for-30 against the Habs.

    After winning Game 5, the Canadiens, led by goalie Jaroslav Halak, would win Game 6 and then completed the shocking comeback by beating the Caps in DC in Game 7.

    The key to this amazing upset was Halak, who stopped 94 of 96 shots fired at him in Games 6 and 7.

    The Canadiens became the first No. 8 seed to ever rally from a 3-1 deficit in a series and defeat a No. 1 seed.

    Halak and the Habs would then go on to upset the defending champion Penguins and Sidney Crosby in another epic seven-game series.

    The amazing run would end against the Flyers, but it all began with the fifth biggest upset in NHL playoff history.

4. 2003 Western Conference Quarterfinals: A Wild Upset

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    As epic a failure as the Capitals' collapse was in regards to our fifth biggest upset, the Colorado Avalanche's collapse against the Minnesota Wild in the 2003 Western Conference quarterfinals can only be called one thing—an epic fail.

    Seeding-wise, this did not look too bad. The Wild were the No. 6 seed; the Avs were the No. 3 seed.

    Where this becomes such a huge upset is when you look at the rosters. The Avalanche were loaded with Hall of Fame players, or future Hall of Famers: Milan Hejduk, Peter Forsberg, Joe Sakic, Adam Foote, just to name a few.

    And they had this guy in goal named Patrick Roy. Yeah, you might have heard of him.

    The Wild were the polar opposites of the Avs. Focusing on defense first (with payroll conservatism a close second), Minnesota was making its first appearance in the playoffs since the NHL granted it an expansion franchise after the North Stars' departure.

    Using a trapping-style defense, the Wild took to the task of grounding the high-flying Avalanche.

    Things started well when the Wild took Game 1 in Colorado. But they would then drop the next three games. Trailing the high-powered Avalanche 3-1, with Game 5 being back in Denver, things looked very grim for the Wild.

    But, somehow, the less talented Wild would win three in a row, including two games on the road, and including two separate 3-2 overtime victories.

    In Game 7, in Denver, Andrew Brunette's overtime winner would cap a remarkable comeback by the Wild—and would also complete the fourth biggest upset in NHL playoff history.

3. 2000 Western Conference Quarterfinals: Singing the Blues

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    The 1999-2000 St. Louis Blues were a really good team. Perhaps not as good as some of the other teams discussed so far, but they did win the President's Trophy with 113 points, and they did it with a more defensive style than one might expect.

    The 1999-2000 San Jose Sharks, on the other hand, were pretty average as they finished with 87 points. They entered the playoffs as the No. 8 seed out West and figured to exit quietly against the mighty Blues.

    But, as we have seen numerous times already, expectations and reality do not always coincide with one another.

    The series started off predictably, with the Blues winning Game 1. From there, however, things got strange. The Sharks won the next three games in a row to take a commanding 3-1 series lead.

    Up until then, the Blues had not lost three games in a row all season long. Obviously, they picked the wrong time to start.

    A key factor in the Sharks' success was the excellent play of their goalie, Steve Shields, as compared to the very shaky play of the Blues goalie, Roman Turek.

    Never was that more evident than at the most crucial moment of the series.

    The Blues had stormed back and tied the series at 3-3. With all the momentum on their side, and having Game 7 at the Kiel Center (now the Scottrade Center), it certainly looked as though St. Louis would avoid disaster.

    Instead, disaster reared its ugly head in the form of a 90-foot slap-shot from Owen Nolan that Turek could not handle.

    The huge mistake by Turek was too much for the Blues to overcome, and the Sharks won Game 7 by the final of 3-1.

    It was a stunning moment in a very crazy series, and the Sharks' upset of the Blues is the third biggest upset in NHL playoff history.

2. 1982 Divisional Semifinals: A King-Sized Upset

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    The Los Angeles Kings' upset of the Edmonton Oilers in the 1982 Smythe Division semifinals is ranked as the greatest upset in hockey history by many others who have done lists such as this. I have it as the second biggest upset in NHL playoff history, and I will explain why in a moment.

    To put into perspective how massive an upset this was, first look at the teams' records. The Oilers finished with a mark of 48-17-15, for 111 points; the Kings finished well below .500 with a record of 24-41-15, for 63 points.

    That is a 48-point difference in points for those keeping track at home.

    Then take a look at the Oilers roster. If you thought the 2003 Avalanche had an imposing lineup, just look at some of the guys the Oilers put on the ice each night: Wayne Gretzky, Mark Messier, Paul Coffey and, of course, Grant Fuhr in net.

    The Kings did not have that kind of talent—not even close. They did have 50-goal scorer Marcel Dionne, but that was about it.

    Meanwhile, Gretzky had scored 92 goals, had 112 assists and racked up 212 points. The Oilers, as a team, scored 417 goals, and there was just no way the Kings could match them.

    Well, as we know by now, never say never.

    The teams would split the first two games, setting the stage for what is known as The Miracle on Manchester.

    In 1982, the Kings played their home games on Manchester Boulevard, and it would be the setting for one of, if not the, greatest comebacks in NHL playoff history.

    The Oilers had a 5-0 lead late in the second period. But the Kings began chipping away at the lead, building momentum and gaining confidence. Trailing 5-3 with just about five minutes left, the Oilers were hit with a five-minute major penalty. The Kings would score to cut the Oilers' lead to one.

    Then, with just five seconds left, the Kings would tie the game as pandemonium ensued on Manchester Boulevard.

    Just a few minutes into overtime, Daryl Evans would notch the game winner, and the Kings seized control of the series.

    Los Angeles would go on to eliminate the Oilers the next game—and therein lies the reason I have this upset, as massive as it is, at No. 2.

    The divisional semifinals were a best-of-five affair back in the early eighties. There are many who feel that had this series been a best-of-seven, the Oilers would have found a way to come back and prevent this upset.

    Nevertheless, the Kings pulled off one of the biggest upsets in NHL playoff history, and virtually everyone agrees with that.

    The Kings would be eliminated in the divisional finals.

    The Oilers would soon become the dynasty of the eighties.

    The two teams would then become involved in the biggest trade in NHL history when Gretzky was traded to the Kings in 1988.

    But in 1982, on Manchester Boulevard, a miracle occurred, the seminal moment in what would become the second biggest upset in NHL playoff history.

1. 2006 Western Conference Quarterfinals: The Oilers Ride the Upset Train

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    While being on the losing end of the second biggest upset on this list, the 2006 Edmonton Oilers were the ones doing the upsetting against the Detroit Red Wings in the biggest shocker in NHL playoff history.

    This series had so much excitement and atmosphere to it, made all the more important by the return to relevance of one of hockey's storied franchises.

    The Oilers had not won a playoff series in eight years, and there was nothing, nothing at all, to suggest that streak would end against the best team in hockey, the Red Wings.

    The Wings had been rather dominant during the 2005-2006, amassing 124 points. And why wouldn't they be? The Wings still boasted one of the deepest, most experienced and most talented rosters in all of hockey.

    With names like Yzerman, Shanahan, Lidstrom, Lang and Chelios leading the way, there was just no way the No. 8-seeded Oilers would be able to compete.

    The Oilers were not a bad team as they tallied 95 points of their own during the regular season. Nevertheless, not many felt the Oilers could challenge the Red Wings.

    The two teams would split the first four games. In Game 5, Oilers goalie Dwayne Roloson would help the Oilers to a 3-2 win that set the stage for Game 6 in Edmonton.

    In one of the best series clinching games ever, the Oilers rallied from a 2-0 deficit to tie the game up. The Red Wings would pull back ahead by a 3-2 score. But again, the Oilers came back to tie the game.

    With just over a minute left, Ales Hemsky connected on a beautifully set-up one-timer, and the Oilers would complete a comeback for the ages and eliminate the best team in hockey in just six games.

    Edmonton was back on the hockey map—and their fans absolutely loved it.

    It would be Steve Yzerman's last game.

    For the Oilers that was just the beginning, though. They would go on to beat the fifth seeded Sharks and the sixth seeded Mighty Ducks to advance to the Stanley Cup Finals, but they would fall short to the Carolina Hurricanes in an epic seven-game series.

    So, why is this the biggest upset in NHL playoff history? What makes it better than the others?

    Obviously, the 29-point difference between the Oilers and Red Wings was a factor.

    The Hall of Fame roster the Oilers were playing against was another huge factor.

    The fact that the series was a best-of-seven affair, as opposed to a best-of-five scenario, also made a difference.

    You also have to look at what that upset led to for Edmonton. Not only did they eliminate the best team in hockey, but they took that one upset, got on the upset train and rode it all the way to the cup finals.

    Before the 2006 Western Conference playoffs, no one outside of Edmonton had any real clue who the Oilers really were.

    After they pulled off the greatest upset in NHL playoff history, though, hockey fans everywhere witnessed for themselves exactly how far grit, determination and confidence will take you.


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