Top 15 Most Heartbreaking Losses In NHL History

“Someone always has to lose.” That’s the bitter reality of sports since they began and will forever be. For every win, someone else has to suffer. What to some fans is a fantastic, stunning comeback is to others a crushing and heart-rending defeat. It’s like that with every fandom and that’s especially true with hockey. This is a sport that relies on back and forth play where momentum can shift at any moment, a team up and riding high brought low in the split second it takes to make a goal. For decades, hockey fans have lived and died on that excitement and every single team fanbase has known how a hard loss can be as no one enjoys a blowout.

But there are the close ones that remain so memorable. The games that were going well in many cases only for a loss to come out of nowhere and deflate you. A defending champion’s bid for a repeat ended or a Cinderella team having the clock strike midnight to end their dreams. It’s sad but it’s inevitable, a hard loss always a hard thing to take. Some, however, are worse than others. The vast majority are playoff losses as those tear the hearts out of fans even more, to see the season end and on a sour note to boot. Here are 15 games that rocked their fans hard and while those on one side can claim them as fine victories, never forget the flip side of how these were bitter failures for others.

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15 Dynasty Deferred

The Chicago Blackhawks are currently the closest the NHL has come to a dynasty in a long time with three Stanley Cup wins in six seasons. However, had one goal gone the other way, the Hawks could have boasted not just one more Cup but joining the elite group to win three in a row. Going in the favorites in the 2014 Western Conference Finals, Chicago took Game 1 only to lose the next three to the L.A. Kings. On the verge of elimination, Chicago fought back to win in double overtime in Game 5 and took Game 6 as well.

Game 7 was at the United Center, a hot affair with back and forth goals, the Hawks holding a 4-3 lead but the Kings managing to tie it up late in the game. The overtime was also tight and wild but Alec Martinez managed to sneak a shot past Corey Crawford to give the Kings the win to advance to the Finals and win the Cup. It was a bitter loss for the hometown Chicago crowd and while the Blackhawks would regain the Cup the next year, their fans are convinced a win here would have enabled them to truly cement the team as a dynasty.

14 Dynasty Ends

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It wasn’t as tight as others on this list but it still hurt for those involved and their fans. For four straight years, the New York Islanders ruled the NHL as Stanley Cup champions, a parade in Long Island turning into an annual event. Sure, they showed some age and losing some of that sharp edge but the Islanders were still considered one of the best in the league and were out for “the Drive for Five” as the 1984 postseason began. It came down to the Islanders and the upstart Edmonton Oilers, led by a young talent named Wayne Gretzky.

Shut out in Game 1, the Islanders roared back to dominate in Game 2 with a 6-1 victory. But from there, it was all Oilers as they would end up winning Game 5 in dominant fashion, 5-2 and earn them their first Cup. It was a sad end to the Islanders’ glory years as they would soon collapse into their infamous bad times while Edmonton rose to become the new powerhouse of the NHL and ended New York’s dreams of another Cup.

13 The Roy Wink

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Despite nagging injuries to Wayne Gretzky and some hard shots, the Los Angeles Kings were still going strong in 1993 to reach the Cup Final for the first time in the franchise’s history against the Montreal Canadiens. The Kings won Game 1 but Game 2 was lost after Kings defenseman Marty McSorley’s stick was deemed an illegal length and a penalty that hit hard. They lost Game 3 as well and then came Game 4 as Canadians goalie Patrick Roy showcased amazing skill and power, catching one Kings shot after another.

When he managed to block a seemingly unstoppable backhand, the cameras caught him winking right at the Kings, showing them he was perfectly fine with whatever they were doing. The Canadians would end up crushing the Kings in Game 5 to win but the series was basically over with that wink and the Kings would have to wait a long time before finally holding that Cup overhead.

12 Bedeviled

After years treated as the joke of the NHL, the New Jersey Devils built themselves up into a franchise able to win three Stanley Cups and as the 2009 Eastern Conference playoffs began, a defensive-minded team able to keep and hold a lead. In the quarterfinals, they had a hard series against the Hurricanes, the Devils confident after a terrific first-place season and fighting hard to push the series to a Game 7 in New Jersey.

Into the third period, the Devils had a 3-2 lead, surely ready to win and move ahead and seemed prepared for the next series. But with 80 seconds left, Jussi Jokinen managed to score to tie the game up. As the clock ticked down, both teams prepared for overtime…before Eric Staal scored with just half a minute left in the game. Thus, the Devils season came to a harsh and sudden end that rocked them to the core and one of the worst for a franchise well used to disappointment.

11 Crushing the Juggernaut

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There’s an entire separate list to be made of teams that were seemingly unstoppable in the regular season but couldn’t close it out with the championship in the end. High on that list has to be the 2010-11 Vancouver Canucks. The best team in their franchise history with 117 points and leading the NHL in goals scored and fewest goals-against, the Canucks were major favorites to win the Cup. They eliminated the Blackhawks, Predator and Sharks and seemed ready to raise the Cup once more as they faced the Boston Bruins. After winning the first two games, Vancouver lost the next two by a combined score of 12-1, combing back in Game 5 but losing Game 6.

So for Game 7, everyone expected the Canucks to react to a home crowd and roar back for a hard-fought battle. Instead, the team that had been so utterly dominant throughout the regular season completely came apart, unable to stop Boston from scoring and hitting at will, the Bruins demolishing them 4-0 to win the Cup. Even worse was that the loss set off massive riots across the entire city, causing millions of dollars in damage and serious bad press.

10 Singing the Blues

The Blues have yet to hoist a Stanley Cup in their 48-year existence. The loss that stings the most has to be 1996 as St. Louis boasted Wayne Gretzky and Brett Hull, a team that surely knew how to pull off some playoff victories. However, that wasn’t enough against the Red Wings as the two teams went to a Game 7 that turned into a scoreless shootout in regulation before the Blues took control in overtime. They had a major advantage, clearly the dominant team yet they just couldn’t seem to get the puck into the net as the Red Wings played them hard.

Finally, Steve Yzerman caught a rebound off of Gretzky’s stick to score the winning goal and advance the Red Wings while poor Blues coach Mike Keenan had to endure a loss in his ninth career Game 7 and probably the hardest playoff loss for a franchise filled with them.

9 A Game of Inches

Football is often called “a game of inches” but in 2004, the Calgary Flames learned the hard way that can pertain to hockey as well. In Game 6 of the Finals, the Flames took on the Tampa Bay Lightning at home, the Flames just needing this win to get the Cup. The game was tied at two late in the third period when Martin Gelinas (who had scored the series-clinching goal in each round of the playoffs) charged to the net, the puck hitting the skate of goalie Nikolai Khabibulin and apparently over the line.

Gelinas celebrated, sure the goal was made but the red light didn’t go off and on various replays, the officials declared that there was no certain evidence the puck had gone over the goal line without Gelinas’ stick also going over it. The Lightning would win in double overtime and then take Game 7 in Tampa Bay, leaving Flames fans to curse over just the difference of just a couple of inches was all standing in the way of the Flames and the Cup.

8 The Easter Epic

In 1987, it was tough to see who could win the Cup but the Washington Capitals were eager to try and led the New York Islanders by a 3-1 semifinals series margin only to drop the next two games. This set up Game 7 in Maryland on Saturday, April 18th. What followed was what remains the longest Game 7 in NHL playoff history as the Capitals took a 2-1 lead late into the third period until the Islanders tied it up with five minutes left. This set up a scoreless overtime. And another. And another. And another.

The fourth overtime began into Sunday morning (Easter Sunday to be exact) and the crowd dwindled. Finally, Pat LaFontaine managed to smack the puck into the Washington net to end the game after 6 hours and 18 minutes. For those Washington fans who hung in there, it was brutal to see the Capitals lose after this long run and closing out an epic clash in rough fashion.

7 Mario’s Fall

In 1993, the Pittsburgh Penguins looked unstoppable and the odds of them winning their third straight Stanley Cup were high. They easily outmached the Devils before facing the Islanders in the Patrick Division finals. The Penguins were up 3-2 but the Islanders managed to win Game 6 and set up Game 7 in Pittsburgh. It was a good back and forth affair with the Penguins outshooting New York 26-11 yet still down 3-1 with just five minutes left in the game.

Pittsburgh bounced back thanks to star Mario Lemieux, scoring twice to tie the game up and send the game to overtime where Pittsburgh had a good record. They were pretty confident and the home crowd was on their side backing them up but with five minutes left in that extra period, David Volek managed to smack a goal in to give the Islanders a stunning upset victory. It was the end of a possible Penguin dynasty.

6 The Head Check

There are plenty of reasons why the Philadelphia Flyers’ loss to the Devils in Game 7 of the 2000 Eastern Conference Finals hurts. First was the fact that the Flyers were up three games to one and should have easily gotten the win to advance to the Cup Finals, an emotional journey considering their coach, Roger Nielson, was fighting cancer. But the Devils managed to come back in the next two games to tie it up and set up a final game in Philadelphia.

The other bad part was Flyers captain Eric Lindros, who had just come back from a concussion, was hit by a nasty head check that sent him to the hospital. The Flyers did their best but with two minutes left in the game, the Devils managed to sneak a goal in to give them the victory and the Philly crowd had to watch the Devils celebrate with the Wales Trophy. To add insult to injury, the NHL fined the Flyers $10,000 for not giving details on Lindros’ injury and the man was soon traded after the season, wrapping up an ugly end to a year.

5 No Goal

It’s been 16 years but nothing makes Buffalo Sabres fans grit their teeth as hard as the 1999 Cup Final. After losing Game 5 to the Stars in Dallas, the Sabres came back home intending to tie the series back up. It was a hard-fought game that turned into a goaltending duel, the score tied at 1 at the end of regulation. Thus, they went into overtime and then a second one, the fans going wild watching this thriller as the two teams went at it hard. It came down to that infamous moment in the third overtime as Brett Hull slapped a rebound into the goal to give Dallas the victory.

That was bad enough for the home crowd but what made it worse was the replay which clearly showed that Hull’s skate was inside the blue paint, a clear violation of the rules. The Sabres team and fans actually sat around for 20 minutes, convinced the goal would be nullified and the game continuing. But it wasn’t and to this very day, whenever the Sabres and Stars clash, you can hear some fans calling “no goal!” out, a reminder of the championship Buffalo fans are convinced should have been theirs.

4 Blowing It All

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After 73 years, it’s still an achievement no NHL team has ever been able to match; blowing a 3 games to none lead in the Stanley Cup Finals. But that dubious honor goes to the 1942 Detroit Red Wings who seemed unstoppable after three wins over the Toronto Maple Leafs. Sure, Toronto won Game 4 with a last-minute goal but that was just a brief gasp. But then the Maple Leafs managed to take the next two games and suddenly, Detroit was in trouble. They held strong into Game 7, looking like they would overcome this minor comeback, holding a 1-0 lead into the third period. Then the Maple Leafs erupted with three straight goals before the Red Wings could even realize it.

It’s still the biggest playoff collapse in NHL history and one of the biggest in all of sports and despite all the Cups the Red Wings have won since, it still sticks in the craw how they basically gave this one away.

3 Meltdown in Beantown

These things could only happen to the Maple Leafs. Years and years of frustration were seemingly going to be offered some reprieve. The Leafs were in their first playoff series since the 2004 lockout and in a first round tilt with division rivals, the Boston Bruins. The Leafs found themselves down 3-1 in the series but fought back to force a Game 7. They jumped ahead to a 4-1 lead in the third period and it seemed like the Leafs would be the toast of Toronto for the first time in an eternity. Who knows, maybe this first round series win would lead to a Cinderella Cup run, right?

Then it all came crumbling down. The Bruins got a goal from Nathan Horton with 11 minutes left to cut the lead to two. Milan Lucic brought it to one with 1:22 left. Just 32 seconds later, Patrice Bergeron would tie the game, then go on to score the winner in overtime. It was a collapse of epic proportions and broke hearts all across Toronto.

2 The Bonehead

A bonafide dynasty, the Edmonton Oilers were going for their third straight Stanley Cup in 1986 and facing off against their arch-rivals, the Calgary Flames in the Smythe Division finals. It was a wild series going to a seventh game in Edmonton, the home crowd ready to cheer their heroes to victory. Smith, a rookie, was called in to fill an injured vacancy and doing his best to handle things as the game built to a 2-2 tie in the final minutes. With the puck passing behind the Oilers net, Smith took it and fired it up, intending to send it up the ice for one of his teammates. Instead, the puck bounced off the skate of goaltender Grant Fuhr and into the net, meaning that Smith basically scored on his own team.

It turned out to be the winning goal to push the Flames onward and Smith (who had celebrated his birthday that very day) stood there, clearly wishing the ice would crack under his feet and swallow him up. He was lambasted by the press and fans although his teammates stood by him in support.

1 17 Seconds

For Red Sox fans, it’s the ball going between Buckner’s legs. For Patriots fans, it’s Tyree’s helmet catch. For Celtics fans, it’s the last minutes of the 2009 Finals. In 2013, the Bruins finally had their own entry worthy of joining those three in the pantheon of Boston sports heartbreakers.

Up 2-1 with only a minute and a half left to play in Game 6of the Stanley Cup Final, the Bruins had dominated the Chicago Blackhawks for most of the game and everyone on both sides were preparing for a decisive Game 7 in Chicago. With Blackhawks goalie Corey Crawford pulled to enhance the attack, the Bruins had things in hand and seemed ready for the win before a home crowd. That was, until Bryan Bickell slammed the puck past Tukka Rask to tie the game up with 76 seconds left. It was a hard move but the Bruins and their fans tried to shrug it off, figuring overtime would have another chance to…

And before that thought could be completed, Dave Bolland nailed a shot into the Boston goal. In the space of just 17 seconds, the Bruins went from the obvious win to down 3-2 and were totally rocked, unable to get back together even with a wide open Hawks net, allowing Chicago to win the Cup. To go from assured victory to utter defeat in record time and before a home crowd as well is still a stunning moment, rocking the Boston sports base hard and standing high on the list of heartbreaking endings in any sport.

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