The chase for the Stanley Cup will begin again very shortly. The start of training camp is just around the corner, and that will be the start of the marathon for 31 teams, including the expansion Vegas Golden Knights.
The new team is pristine, filled with hope and no painful memories. They have yet to make a mistake that anyone can look back on and say it cost them a Stanley Cup. While they made plenty of moves in their first offseason, there’s no way of knowing yet whether they made good moves or bad moves. However, the other 30 teams cannot say the same thing.
The Montreal Canadiens have won a record 24 Stanley Cups, but none have come since 1993, and they have made key mistakes that have cost them potential championships. So has every other team in the league. In fact while you could make an argument about there being parity in the NHL, the bottom line is, since the lockout only seven different teams have won the Stanley Cup since the 2004-05 lockout, with Pittsburgh, Chicago and L.A. winning multiple Cups in that span. Only one team can win every year and this list is a painful reminder of that.
We look at each team’s worst mistakes and most painful moments in this feature.
30. Anaheim Ducks: Shellacked At Home In Game 7
The 2013-14 Ducks were something of a dynamo in the NHL’s regular season. They rolled to first place in the Western Conference with 116 points and were just a point behind the Boston Bruins for the Presidents’ Trophy.
Head coach Bruce Boudreau expected a long run in the Stanley Cup playoffs. After beating the Dallas Stars in six games in the first round, the Ducks found themselves in an 0-2 hole after losing the first two games of their second-round matchup at home with the rival Los Angeles Kings.
The Ducks rebounded with three straight wins and clearly had the momentum, but lost a 2-1 decision at the Staples Center in Game 6 and got blown out 6-2 at home in Game 7.
Instead of rolling into the Stanley Cup Final, the Ducks got punched in the gut and were sent home in the second round. It continued an awful trend for the Ducks of losing Game 7 on their home ice that had started the year before against the Detroit Red Wings.
29. Arizona Coyotes: Missed Call Leads To Penner’s OT Winner
It’s been a difficult assignment for the Coyotes to establish a foothold in the desert since the franchise left Winnipeg following the 1995-96 season. It seems the franchise has been on the brink of leaving Arizona on a regular basis as the team searches for the best location and a new, hockey-friendly arena.
The Coyotes have struggled badly in recent years, but they have had some decent teams in the past. Perhaps their biggest opportunity came in the 2012 Stanley Cup playoffs when the Coyotes rolled to wins over the Chicago Blackhawks and Nashville Predators in the first two rounds.
All that stood between the Coyotes and their first trip to the Stanley Cup Final was the Los Angeles Kings. Instead of rolling over the Kings, head coach Dave Tippett and forward Shane Doan got pummeled in five games and their run came to an abrupt halt. In Game 5 overtime, Kings captain Dustin Brown got away with an elbow and Dustin Penner would score moments later to eliminate the Yotes.
28. Boston Bruins: Everything Falls Apart In 17 Seconds
The Bruins have six Stanley Cups to their credit, but heartbreak has been associated with this franchise for decades.
The arch-rival Montreal Canadiens won every playoff series between the two teams for a 45-year period that didn’t end until 1988. While the Bruins have held their own against the Habs since then, they absorbed a brutal second-round defeat in 2014 after winning the Presidents’ Trophy.
However, the 2013 Stanley Cup Final loss to the Chicago Blackhawks was even worse. They lost Game 1 on the road in triple overtime after having a two-goal lead midway through the third period. Teams that want to win the Stanley Cup Final don’t blow multiple-goal lead in the final 20 minutes.
The Game 6 loss that gave Chicago the Stanley Cup saw the Bruins allow two goals within 17 seconds in the final moments. Instead of forcing Game 7, the Bruins had to watch the Blackhawks skate around the TD Garden with the Stanley Cup.
27. Buffalo Sabres: No Goal
The Buffalo Sabres have not been to the Stanley Cup playoffs since the 2010-11 season. While there is some hope for the future thanks to the likes of Jack Eichel, the Sabres have been relatively awful at finding talent in the draft, and that’s why they have endured a long dry spell.
The city of Buffalo has had to endure a lot of heartbreak, first with the Buffalo Bills losing four straight Super Bowls, then to see their Sabres push the Stars to six games in 1999, only for a controversial call to decide it all. There are those that dispute Brett Hull’s foot being in the crease was legal, as the NHL had changed the rules earlier that year, but some say the NHL never communicated that. Either way, this was a true heartbreaker for Buffalo.
26. Calgary Flames: Gelinas No-Goal and Releasing St. Louis Comes Back To Haunt Them
The Flames have had their moments in the NHL, including a trip to the Stanley Cup Final in 1986, and their only Stanley Cup championship in 1989. Veteran Lanny McDonald scored the Stanley Cup clinching goal against the Montreal Canadiens, and Flames fans are still smiling over that one.
The biggest mistake came in 2000 when they parted company with Martin St. Louis. He would eventually earn a Stanley Cup as a member of the Tampa Bay Lightning, and St. Louis would prove to be a superstar in central Florida.
Craig Button was the general manager of the Flames at the time, and he deemed St. Louis too small to be an impact player in the NHL. St. Louis would score 365 goals and 953 points in 972 career regular-season games and his Lightning would beat the Flames in 2004. We all remember that Cup Final for the controversial goal/no-goal scored by Martin Gelinas in Game 6 of that series. St. Louis would score in overtime of that game to force Game 7, and the Flames lost their best chance at a Cup in decades.
25. Carolina Hurricanes: Overtime Streak Ends In ’02 Final
The Carolina Hurricanes pulled off one of the greatest shockers in NHL history when they won the 2006 Stanley Cup, beating the equally surprising Edmonton Oilers in seven games.Peter Laviolette was the head coach of this feel-good story, and it seemed the Hurricanes had established a place for themselves on Tobacco Road in the heat of basketball country.
However, four years earlier, the Hurricanes let a golden opportunity slip through their grasp. The Canes had the heavily favored Detroit Red Wings deadlocked at 1-1 in the 2002 Stanley Cup Final, and held a 2-1 lead in the closing moments of Game 3, only to allow a late game tying goal by Brett Hull. The Wings would outlast the Canes, winning on an Igor Larionov 3OT goal. Had the Canes held on in that game, they very well could have had their first cup back in ’02.
24. Chicago Blackhawks Fall To Montreal On Home Ice In Game 7
The Chicago Blackhawks have certainly hit their stride with three Stanley Cups since 2010, and they are in the running to become the team of the decade along with the Pittsburgh Penguins.
However, the Blackhawks endured quite a bit of pain between their Stanley Cup in 1961 and their next one in 2010. The worst pain came in 1971, when they faced the Montreal Canadiens in the Stanley Cup Final.
Chicago had a 2-0 lead in Game 7 at the Chicago Stadium as the game passed the halfway point. However, the game turned when Montreal’s Jacques Lemaire blew a slapshot from just over center ice past goalie Tony Esposito. Henri Richard scored the next two goals, and the Habs skated around the Chicago Stadium with the Stanley Cup.
23. Colorado Avalanche: Blowing A 3-1 Series Lead To Edmonton
The Avs won the Pacific Division in the 1997-98 season as they were led by Joe Sakic and Peter Forsberg. They appeared to have a relatively easy first-round matchup with the Edmonton Oilers, who lost more games than they won during the regular season.
The Avs built a 3-1 lead in the series and it appeared they would cruise on to the second round. But the high-scoring Avalanche suddenly stopped scoring against the Oilers. They dropped a 3-1 decision at home in Game 5 and were blanked in both Game 6 and 7 as their season came to an abrupt halt.
22. Columbus Blue Jackets – Playoff Woes
The Blue Jackets have been playing hockey since 2000, and they have made the Stanley Cup playoffs just three times in their history.
They have not won a playoff series, having lost twice to the Pittsburgh Penguins and once to the Detroit Red Wings.
We can’t point to any one mistake that has cost the Jackets the Stanley Cup, and we can’t really say which of their playoff losses were the most heartbreaking. But their misfortune is that they have had to play one Stanley Cup Finalist in the Red Wings (2010), one Stanley Cup winner in the Penguins (2017) and a powerful 109-point team in the Pens (2014).
21. Dallas Stars: Jason Arnott Ends Their Hopes Of A Repeat
When Brett Hull tucked a short shot past Dominik Hasek of the Buffalo Sabres in overtime of the sixth game of the 2000 Stanley Cup Final, the Dallas Stars won their first Stanley Cup in a team history that goes back to the original 1967-68 expansion when they were the Minnesota North Stars.
They were nearly as strong the following year when they reached the Stanley Cup Final against the New Jersey Devils.
While they fell behind the Devils 3-1 in the series, the Stars won Game 5 in New Jersey by a 1-0 margin in triple overtime. That gave the Stars momentum as they returned home for Game 6.
That game also went into overtime, but the Devils ended the series when Jason Arnott was left alone in front of the net and beat Ed Belfour in the second extra period. The Stars never should have left the opportunistic New Jersey forward in front of the net unchecked, and it cost them the Stanley Cup.
20. Detroit Red Wings: Lidstrom Stopped At The Horn
The Detroit Red Wings were the defending Stanley Cup champions in the 2008-09 season, and there was no reason to think that the Mike Babcock-coached team would not win a second consecutive Stanley Cup. The Red Wings rolled to the Presidents’ Trophy with 112 points and they would meet the Pittsburgh Penguins for the second year in a row in the Stanley Cup Final.
The Red Wings jumped to a 2-0 lead in the series, and while the Pens fought back to tie the series at 2-2, it appeared the Red Wings would roll after recording a 5-0 win in Game 5. However, the Pens bounced back to take the Stanley Cup with wins in Game 6 and 7. Nicklas Lidstrom nearly tied it in the final seconds, but Marc-Andre Fleury would stop his last-second shot and the Red Wings were denied back-to-back NHL titles as they let the series slip away.
19. Edmonton Oilers: Steve Smith’s Own Goal
A look at the NHL history book reveals the Oiler won four Stanley Cups in five seasons between 1984 and 1988. The only year that they didn’t win in that span was 1986, when they were beaten in the second round by the Calgary Flames in seven games.
While the Flames were a competitive team that year, the Oilers scored 119 points and were heavy favorites. The Flames pushed the Oilers to the limit, and the seventh game was tied 2-2 late in the third period.
That’s when solid defenseman Steve Smith made the play he would like to forget. As he came around the net, he mistakenly slid the puck into his own net, giving the Flames the lead and the series win. Smith was one of the most beloved of his teammates, and they rushed to console him, but that mistake has become a part of his legacy.
18. Florida Panthers: Swept In Lone Finals Appearance
The Panthers have been to the Stanley Cup Final once, and they were clearly the second-best team as they dropped the 1996 Stanley Cup Final to the Colorado Avalanche in four straight games.
The Panthers would have likely needed divine intervention to get a different result, but they might have made it tougher on the Avs if they could have made an early lead in Game 1 stand up.
Florida got on the board first as Tom Fitzgerald scored a first-period goal off a feed from Bill Lindsay. The lead held up until the midway point of the second period, and that’s when the Avs responded with three goals in less than four minutes.
17. Los Angeles Kings: Marty McSoreley’s Stick
The Los Angeles Kings have won two Stanley Cups during the current decade, and those championships are clearly the biggest achievements in franchise history.
However, one bad break in the 1993 Stanley Cup playoffs may have prevented them from winning their first Stanley Cup quite a bit earlier.
The Kings got on a roll in the ’93 playoffs, beating the Calgary Flames, Vancouver Canucks and Toronto Maple Leafs in the first three rounds. They earned a spot in the Stanley Cup Final against the Montreal Canadiens, and after winning Game 1 at the Montreal Forum, the Kings led Game 2 by a 2-1 margin late in the third period.
That’s when Montreal head coach Jacques Demers played his cards perfectly. He asked the referees to measure the curve on Marty McSorley’s stick. When it was ruled illegal, the Habs went on the power play and Eric Desjardins scored to tie the game. He later won the game in overtime.
16. Minnesota Wild: Offense Dries Up Against The Blues
The Wild made the Western Conference Finals in their third year, but that was largely viewed as a fluke because the team had quite a few holes.
The Wild were a much better team in 2016-17, as they finished with the second-best record in the Western Conference. The Wild had 106 points during the regular season, and seemed ready to go on a long postseason run.
However, the Wild picked the wrong time to go into a slump. Zach Parise and Co. scored just one goal in each of the first three games and fell into an 0-3 hole. The Wild rebounded with a desperation win in Game 4 and pushed Game 5 to overtime, but that’s where the season came to an end.
15. Montreal Canadiens: Losing Carey Price In Game 1 Of 2014 ECF
No team is close to the Canadiens’ remarkable total of 24 Stanley Cup titles. However, Les Glorieux have not brought home a championship since 1993, and the natives are more than a little restless.
The Habs have not even been back to the Stanley Cup Final since their last title, but the 2013-14 Habs should have either won or gotten to the final. Montreal had just upset the top-seeded Bruins in the second round and had home ice advantage over the Rangers in the Eastern Conference Final, but all their hopes disappeared when Carey Price suffered a knee injury in Game 1.
There’s debate as to whether Chris Kreider slid into Carey Price on purpose or if it was defenceman Alexei Emelin’s stick that caused Kreider to fall. Either way, the Habs lost their meal ticket and they would fall to the Rangers in six games.
14. Nashville Predators: Sissons Denied A Possible Game Winner In Game 6
Prior to the 2017 Stanley Cup playoffs, the Nashville Predators were viewed as a try-hard team that simply didn’t have enough talent to get past the second round.
Head coach Peter Laviolette was sick of that assessment, and he motivated his team to find another level in the postseason. The Preds shockingly swept the Chicago Blackhawks, and followed with impressive wins over the St. Louis Blues and Anaheim Ducks to earn a spot in the final against the defending champion Pittsburgh Penguins.
The tone was set in the first two games in Pittsburgh. The Preds controlled play for long periods in both games, and could have won either, but they failed to come up with a win. They rallied from a 3-0 deficit in Game 1 before losing 5-3, and were tied at 1-1 after two periods in Game 2 before losing 4-1.
While Nashville rallied to tie the series at home, the Pens took advantage of home ice in Game 5 and a Colton Sissons goal was disallowed in Game 6 because the referee blew the whistle too early. The game changed and the Pens would score the Cup winner with just over a minute left in the game, costing the Preds a chance at a Game 7.
13. New Jersey Devils: Blow 3-2 Series Lead And Chance To Repeat
The 2001 Stanley Cup Final between the Devils and the Colorado Avalanche is one of the most memorable matchups in NHL history.
The Avs featured stellar defenseman Ray Bourque, who was in the last season of his brilliant 22-year career. He had never been a part of a Stanley Cup winner with the Boston Bruins and he moved on to the Avs the season before with the hope of winning a championship.
The Avs got on a roll and met the Devils in the 2001 Stanley Cup Final. New Jersey featured Patrik Elias, Petr Sykora, Scott Stevens and goalie Martin Brodeur, and the Devils were the defending Stanley Cup champions.
New Jersey held a 3-2 lead and had a chance to finish the series with a win at home, but the Avs rolled to a 4-0 road win.
The Devils came up short in Game 7, as Colorado won the Stanley Cup after taking Game 7 by a 3-1 margin.
12. New York Islanders: Run Out Of Gas In ’93 Run
The Islanders had one of the great dynasties in league history, having won four straight Stanley Cups from 1980 through 1983.
After getting to the finals and handing the dynasty baton to the Edmonton Oilers the next year, the Islanders have become one of the more irrelevant franchises in the league.
The 1992-93 Islanders were the last Isles team to win a playoff series for 23 years. That year, the Isles managed to miraculously reach the third round of the playoffs, after knocking off the heavily favored Penguins on a Billy Volek overtime goal in Game 7. However, they were out of gas by the next round, as they lost two overtime games to Montreal in a five-game series loss.
11. New York Rangers: Alec Martinez Ends Miracle Run
Rangers fans of a certain age still hear the chant in their sleep. “1940, 1940” was all the team and its fans had to hear in the 1970s, ‘80’s and early ‘90’s to remind them of their last Stanley Cup. While not Chicago Cub-like, it was painful.
That ended in 1994 when the Rangers finally ended their 54-year drought by beating the Vancouver Canucks in seven games. That memory has lasted for the Rangers, and it must because they have not won another title since then.
They reached the Stanley Cup Final in 2014, but after recording wins over the Philadelphia Flyers and Pittsburgh Penguins in back-to-back seven-game series, they made it to the Stanley Cup Final by beating Montreal – without Carey Price – in six games.
10. Ottawa Senators: Magic Runs Out In Game 7
The Ottawa Senators made it to the Stanley Cup Final in 2007 where they fell short against the Anaheim Ducks, losing the series in five games.
However, the Sens’ best chance to win the Stanley Cup may have been last season. With stellar defenseman Erik Karlsson at the top of his game, and goalie Craig Anderson coming up with clutch stops, the Sens beat the Boston Bruins in six games and the New York Rangers in six.
They met the defending champion Pittsburgh Penguins in the Eastern Conference Final, and extended Sidney Crosby & Co. to overtime of the seventh game. Chris Kunitz ended matters with the last goal of the series, and the Sens were left wondering what might have been after watching the Pens win the Stanley Cup two weeks later by beating the Nashville Predators.
9. Philadelphia Flyers: Kane’s Ghost Goal
Did Patrick Kane’s shot go into the net or not?
That was the question that the hockey world was asking after the 2010 Stanley Cup Final between the Chicago Blackhawks and Philadelphia Flyers. Kane celebrated as he knew he had scored the Cup-winning goal, but nobody else seemed to get it.
Subsequent replays showed the puck under the collar of the goal, and that Kane had indeed scored the winner and broken the hearts of the Flyers, who lost the series in six games.
Prior to that loss, the Flyers had beaten the Buffalo Sabres, Boston Bruins and Montreal Canadiens to reach the championship round. The win over the Bruins was particularly satisfying, since Boston built a 3-0 lead before the Flyers stormed back to take the series in seven games.
8. Pittsburgh Penguins: Experience Prevails Over Youth
The Penguins have won three Stanley Cups in the Sidney Crosby era, including back-to-back championships the last two seasons.
Crosby’s first title came in a seven-game triumph over the Detroit Red Wings in 2009, but the Pens lost the Stanley Cup Final the year before to those same Wings.
The Penguins had rolled over the New York Rangers in four games, and then defeated the Ottawa Senators and Philadelphia Flyers in five games before meeting the veteran Wings.
Detroit took a 3-1 advantage before the Pens won Game 5 by a 4-3 margin in triple overtime at Joe Louis Arena on a goal by Petr Sykora. The Red Wings broke Pittsburgh hearts in the next game, but the Pens would use that defeat as fuel the following season.
7. San Jose Sharks: Fall Short In Final
After years of playoff disappointment, the Sharks finally reached the Stanley Cup Final in 2016.
The Sharks had asserted themselves against the Los Angeles Kings, outlasted the Nashville Predators and gotten the best of the St. Louis Blues to earn their way into the championship round against the Pens.
This was a huge victory for a franchise that included Joe Thornton, Patrick Marleau and Brent Burns, and had long been associated with choking.
They wiped that image out in the first three rounds, but the Pens won the series in six games, leaving the Sharks to contemplate their shortcomings once again. The Sharks had their chances, as they forced overtime in Game 2 and got great goaltending from Martin Jones all series, but they lost the final on home ice.
6. St. Louis Blues: The Blues’ Window Closes
The Blues benefited from the NHL’s playoff system in their first three years, as they proved to be the class of the expansion teams in 1968, ’69 and ’70 – at least as far as the postseason was concerned – and made the Stanley Cup Final each year.
However, the Blues could not win a single game in two years of Stanley Cup Final competition against the Montreal Canadiens and one year against the Boston Bruins.
The Blues have not been back to the championship round since. However, the Blues made it to the Western Conference Final in 2016, but fell short against the Sharks.
5. Tampa Bay Lightning: Offense Dries Up In ’15 Final
Head coach John Tortorella and the Lightning won the 2004 Stanley Cup by beating the Calgary Flames in seven epic games. Martin St. Louis, Vincent Lecavalier and Brad Richards simply would not let the Lightning lose, and the team won the only title in its history.
However, Tampa Bay has come close since. The Lightning reached the Stanley Cup Final in 2015 against the Chicago Blackhawks, and took a 2-1 lead in the series after three games. However, Tampa Bay’s offense dried up after that, scoring just two goals in the final three games.
4. Toronto Maple Leafs: Gretzky’s High Stick Missed By Kerry Fraser
The Maple Leafs have known little besides pain since winning their last Stanley Cup in 1967.
While a new generation of Leaf players are trying to restore the franchise’s luster, the team has often known heartbreak since.
The Maple Leafs were one game from reaching the Stanley Cup Final in 1993, but they lost the final two games of the Western Conference Final against the Los Angeles Kings. Wayne Gretzky has called his seventh-game performance in that series – three goals and an assist – the best of his career.
It was a brutal defeat for the Leafs, and they have not been as close to the top of the NHL’s mountain since. Drawing a matchup like the Canadiens in that year’s cup final would have been a favorable one for Toronto, and they likely would have ended their drought.
3. Vancouver Canucks: 2011 Magical Run Ends
The hard-luck Canucks have been to the Stanley Cup Finals twice in their history, and both resulted in crushing seventh-game defeats.
The Canucks served as the opposition to the New York Rangers when they broke their 54-year slump and won the 1994 Stanley Cup. The Canucks trailed 3-1 in the series, but won Games 5 and 6 to force a decisive game. New York was slightly better in coming away with a 3-2 victory.
The pain may have been worse in 2011, when they dropped a seven-game series to the Boston Bruins. The first six games went to the home teams, and since Game 7 was in Vancouver, the Canucks appeared to have the edge. However, the Bruins received two goals from Patrice Bergeron and two more from Brad Marchand, and Tim Thomas provided shutout goaltending.
2. Washington Capitals: Best Team In Franchise History Falls Short
The Caps have been one of the most heart-breaking franchises in the last 10 years, often dominating in the regular season only to come up short in the playoffs.
The Caps have made it to the Stanley Cup Final just once in their history, losing in four straight games to the Detroit Red Wings in 1998. However, the Caps may have had their best team in 2015-16.
Washington won the Presidents’ Trophy with a 56-18-8 record that produced 120 points. Despite their regular-season dominance, they struggled to get past the Philadelphia Flyers in six games in the first round.
1. Winnipeg Jets: Get Swept In First Playoff Berth Back In WPG
The most heartbreaking loss in Winnipeg Jets’ history would be well, losing the team altogether, however we are going to focus on the new Jets here. The Jets came back to Winnipeg in 2011, but this time it was the Atlanta Thrashers’ original franchise that moved north and adopted the name that the city had grown to love. The Jets have only made the playoffs once since their move and that came in 2015 where they took on the Anaheim Ducks. The Jets were able to keep the games close, but ultimately, they couldn’t register a win over the top seeded Ducks. Despite the sweep, the Winnipeg faithful gave their Jets a standing ovation, but you have to think they’ll want to see some playoff success soon.
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