Top 15 Greatest Moments in NHL Playoff History

The Stanley Cup Playoffs are an unparalleled grind. The NBA and MLB postseasons have their moments and the NFL has its fair share of guts and grit, but nothing compares to the two months of unbridled passion and determination that characterizes the quest for Lord Stanley’s mug. And from this quest springs moments that have forever defined the game. From Messier’s guarantee to Orr flying through the air to Toronto’s epic 3-0 comeback in 1942, the NHL Playoffs have it all. And the proof of this never-say-die attitude is there. In the history of the NBA, no team has ever come back from down 3-0 to win a seven game series. In the history of the MLB, only the 2004 Boston Red Sox have accomplished such an unlikely feat. And in the history of NHL, four teams have climbed out of the cellar to such improbable heights (Toronto in the 1942; the New York Islanders in 1975; Philadelphia in 2010 and Los Angeles in 2014).

Everyone remembers Joe Namath’s famous guarantee of victory over the Baltimore Colts, though it was Mark Messier who redefined (and arguably revolutionized) this type of Big Apple guarantee in 1994. Reporter John Giannone wrote at the time that, “The questions that elicited Messier’s response had little to do with a prediction. But Messier’s replies were pointed and direct. They were as clear as the Champagne the Rangers still hope to drink from the Stanley Cup in the coming weeks. And they carried a distinct message from the weary leader to the embattled troops: I’ve put my five Stanley Cup rings, my reputation and my neck on the chopping block, boys. Now save me.”

There is a certain type of magic to the MLB’s October Classic. The NBA Playoffs have had some epic buzzer beaters. And no one can question the unmatched excitement that surrounds last-minute drives during the Super Bowl. But in terms of sheer will to succeed over a prolonged period of time, the Stanley Cup Playoffs cannot be beat.

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16 Steve Smith's Own Goal

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The Edmonton Oilers could've very well been the second team in NHL history to win five straight Stanley Cups if not for Steve Smith's own goal in Game 7 of the Campbell Conference Semifinals. With the game tied, Smith was attempting to push the puck up the ice from behind his net, but caught the back of his goalie's skate, sending it into the net.

The gaffe ended Edmonton's quest for a three-peat, although they'd win two championships in 1987 and 1988. This gap in 1986 was all that separated them from a possible five straight championships.

15 Petr Klima Ends Longest Game In Finals History

The longest game in the history of the Stanley Cup Finals deserves a mention. Not only was Game 1 of the 1990 Stanley Cup Final the longest game in the history of the finals, it included a power failure in the building, prolonging the game further.

The Oilers and Bruins were squaring off in a rematch of the 1988 final. This time, the Oilers were without Wayne Gretzky and the Oilers' dynasty was reaching its end. The Bruins were trying to win their first Cup in 18 years and give their already legendary defenceman Ray Bourque his first. The series began with a triple overtime marathon.

The score was tied at two in overtime, and wouldn't end until 1:22 in the morning, after 115 minutes and 13 seconds of hockey. Early in the third overtime, there was a 25-minute delay due to a power failure. All the extra rest did well for Petr Klima, who had been benched most of the overtime. Klima came off the bench late in the sixth period and squeezed a puck through Andy Moog to give the Oilers the game. They would win the series in five to complete their dynasty.

14 No Goal?

It might be one of the most controversial moments in NHL history, but it's also one of the most memorable, so it deserves a spot. The Dallas Stars and Buffalo Sabres were in triple overtime of Game 6 in the 1999 Stanley Cup Final. The Stars were trying to win their first Stanley Cup in franchise history, while the Sabres were trying to force a Game 7 back in Dallas.

Brett Hull grabbed a rebound in front of Dominik Hasek and with his foot in the crease, buried the puck for the winner. NHL rules at the time prohibited players from scoring while in the crease, although Hull has said that the NHL had amended that rule earlier in the season via a memo. Either way, no one has forgotten about this moment.

13 Montreal Wins Fifth Consecutive Cup

via habseyesontheprize.com

The standards for which we label a dynasty nowadays have greatly diminished. In the salary cap era, we are likely never going to see a true dynasty. Runs like the Chicago Blackhawks and Los Angeles Kings winning two Cups within a few years are likely as close as we'll come.

The Montreal Canadiens closed out the 50s with five straight Stanley Cups. When you're able to fill an entire hand with rings over a five-year period, that's a remarkable achievement. The Habs closed their run with a series win over the Toronto Maple Leafs. This dynasty established Montreal as the most decorated franchise in the NHL.

12 Gretzky’s Get-Away

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His son Kerry had just blown the most important call in his career as a NHL referee and fans were cursing his child’s name. The Great Gretzky had clearly high-sticked Wendel Clark in overtime and, minutes later, netted the Game 6 winner in overtime. It was the early morning of May 28th, 1993 and the late Hilton Fraser had just gone to bed as one irate Leafs’ fan traveled hundreds of kilometers from Toronto to Sarina and began smashing his car into the family’s tiny mobile home. Hilton, an ex-boxer, grabbed his trusty axe and ran the criminal off his property. A true professional to the end, Kerry Fraser acknowledges he blew the call and confesses, I worked 2,165 NHL games and that probably was my worst moment… I strive for perfection in everything I do. On that day, I wasn’t.” Fraser’s mother still fields midnight phone calls from livid Leafs’ fans and blows the very whistle Kerry used from that game into the phone, blasting the caller with a piercing screech. A truly fitting punishment for bitter Leafs’ fans that just can’t let go of the past.

11 The Comeback

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The Maple Leafs were not only the first team to come back from down three games to none, but the only team to do so in the Stanley Cup Final. The series had everything, including the tossing of a woman’s shoe onto the ice and a brawl between famed Detroit coach Jack Adams and referee Mel Harwood after a raucous and controversial fourth game. Harwood and NHL President Frank Calder had to be escorted out of the arena under police escort and Calder subsequently suspended Adams indefinitely. After the Game 7 comeback was complete, Leafs head coach Hap Day joked, “We won it the hard way.”

10 Mission 16W Completed


Raymond Bourque had everything he could have ever dreamed of on his NHL resume after two decades with the Boston Bruins: five Norris Trophies; a Calder and a team captaincy to his name. However, hockey’s greatest prize had always eluded Bourque in spite of two Cup appearances in 1988 and 1990. In March of 2000, Bourque had the chance to move to a legitimate contender in Colorado and eventually decided to take that chance. Bourque dubbed his goal of hoisting the Cup as ‘Mission 16W’, which he accomplished in 2001, before promptly retiring on top of the hockey world. The indelible image of Bourque lifting the Cup is perhaps only surpassed by Bobby Orr’s superman impersonation.

9 The Curse of Bill Barilko

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Hailing from the frigid and remote northern most tip of Ontario, Bill Barilko always harbored dreams of playing for the Maple Leafs. In his short time wearing the blue and white, Barilko won four Stanley Cups in just five seasons. In his final season in 1951, the Leafs faced off against their legendary rival the Montreal Canadiens. Toronto ended up taking it in five games and the series became the first and only final that saw every game go to overtime, with Barilko netting the series clincher.

Tragedy struck that summer as Barilko’s plane went down after a fishing trip in Northern Ontario. The Leafs didn’t win a cup again until 1962, shortly after pilot Ron Boyd discovered Barilko’s body. The curse of Bill Barilko had ended, but his legacy was not soon forgotten.

8 Foggy Bottom

The 1975 Stanley Cup Final between the Philadelphia Flyers and Buffalo Sabres was unique for a variety of reasons. For one, it was the first time two non-original six team played in the Finals. It was also the last time a team comprised solely of Canadian-born players would win the Cup. Finally, and most bizarrely, Game 3 was played in a thick fog due to the abnormal Buffalo heat in May of that year and a lack of air conditioning inside the arena. In a desperate and futile attempt to try to dissipate the fog, rink officials skated around the ice with bed sheets in between whistles.

The oddest incident though occurred after a bat got into the arena and flew around the players for the majority of the game until Buffalo centre Jim Lorentz swatted it with his stick, making him the first and only player in NHL history to kill an animal during a game. Many Buffalo fans still refer to this incident as the “Evil Omen” and blame this supposed curse for Buffalo’s eventual defeat in the series.

7 Orr’s Iconic Image

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Though it’s hard for a writer to admit, pictures are worth a thousand words. However, it must be remembered that Bobby Orr’s iconic overtime goal in 1970 capped off a sweep of the St. Louis Blues and a series that was really over by Game 4. Photographs can lie as easily as words can. Having said that, Ray Lussier’s image of Orr sailing jubilantly through the air and the simultaneous look of disgust on Blues’ defenceman Noel Picard’s face says it all. It is undoubtedly one of the most famous goals in hockey history and delivered the Bruins their first Stanley Cup in almost 30 years. As Bobby tells it, I looked back, and I saw it go in, so I jumped.”

6 The Legend of Bobby Baun

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No other player in the history of hockey, with the exception of Paul Henderson, is known for his incredible performance during one, solitary game. In the third period of Game 6 of the 1964 Stanley Cup Final, Boomer broke his leg after being hit by a Gordie Howe slapper. After a dose of painkillers and a quick tape job, the Leafs defenceman came back into the game and scored the overtime winner. Baun would go on to play in Game 7 on his broken leg and help the Leafs to victory. In another memorable game, as a coach of the Toronto Toros, he fined each member of his team $500 when they lost a game 10-9 after blowing an 8-2 lead. He refunded the money, but was still fired.

5 Six Boston Skaters, Four Straight Montreal Cups


It's a moment that's relived every time Canadian viewers tune into Coach's Corner on Hockey Night in Canada. The Boston Bruins were minutes away from pulling off an incredible upset over the Montreal Canadiens who had dominated the 70s, having won three straight Stanley Cups (1976-78) and five in the decade up to that point.

The Bruins were up 4-3 in the dying moments of Game 7 in the 1979 Stanley Cup semifinal. Boston was then caught with too many men on the ice, giving the vaunted Canadiens offence a power play with under three minutes left. Usually when you give great teams a gift, they gladly take it and shove it back in your face. That's exactly what Montreal did, as Guy Lafleur fired a bullet past Gilles Gilbert to tie the game.

Yvon Lambert then put the Bruins away in overtime and the Habs then won the final in five games to win their fourth Stanley Cup, closing out the 70s with style.


3 Le Mieux

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Darryl Sittler’s record of 11 points in one game will likely never be shattered, but Mario Lemieux undoubtedly holds the record for greatest individual performance in a postseason game. In Game 5 of the 1989 division finals, Lemieux’s Penguins faced off against their inter-state rivals from Philadelphia. After just seven minutes of hockey, Lemieux already had netted a hat trick. By the second intermission, Lemieux had tallied four goals and three assists. His empty netter sealed the deal and helped Pittsburgh garner a stunning 10-7 victory, though they would eventually go on to lose the series in seven games.

2 Messier Channels Namath

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It ain’t bragging if you back it up. And Mark Messier certainly backed up his words with his actions. With his Rangers down 3-2 in the Eastern Conference Finals in 1994 and in search of their first Stanley Cup in 54 years, Messier injected a bolt of confidence into his floundering team and guaranteed a victory in Game 6. The defenseman came out firing and would eventually pot a hat trick.

As the New York Times pointed out, “Joe Namath needed a few booster shots of Scotch before he blurted his in response to a heckler at a Miami Touchdown Club banquet the Thursday before the Super Bowl against the Colts, the prohibitive favorites. Even the New York tabloids all but ignored [the guarantee] until after the Jets had pulled off the stunning upset and then burnished it into legend.”

Messier stuck his neck out with intent and didn’t need any liquid confidence to do it. Though he wasn’t the first purveyor of the sports guarantee, he is arguably the greatest.

1 Three for the Price of One

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It was 2:25 am in the morning on March 25th, 1936 at the Montreal Forum and one of the most epic games in NHL history was reaching its climax. Almost 180 minutes of hockey had been played between the Detroit Red Wings and the Montreal Maroons. Fans were asleep in their seats- literally. Detroit netminder Normie Smith had remained unbeaten after 90 saves, though the eventual hero would be rookie Modere “Mud” Bruneteau, a man who still held his position as a clerk in a Winnipeg grain office, and who scored the game’s only goal in the ninth period of play.

Smith estimates he lost 12 pounds during the game, just from sweat alone. In total, almost three tons of snow was shoveled and removed between periods. A newspaper advertisement described a match where, “The boys were so tired they were skating from memory and shooting by ear. The referees were so weary they could only blow feeble toots on their tin whistles.” The game still stands to this day as the longest game in NHL history.

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