Every fan must endure bitter defeat from time to time, but when it comes to choosing the most painful loss ever suffered by a team there are many factors to consider: the expectations, the opponent, the stakes. Blowout losses hurt, but it’s the close ones—the ones that got away, or the ones that were decided by fickle fate—that are often the most memorable.
This series revisits each NHL franchise’s worst gut-punch defeats. Here is Part 1:
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• Toronto Maple Leafs: May 13, 2013; Eastern Conference Quarterfinals Game 7—Bruins 5, Maple Leafs 4 (OT)
Ever-optimistic Toronto fans have endured more than their share of heartache since the Leafs won their last Stanley Cup in 1967, but it’s hard to top this brutal loss. Expected to finish near the bottom of the Eastern Conference, Toronto instead made its first playoff appearance since 2004. Hope blossomed when Boston squandered a 3–1 series lead. By Game 7, the Bruins were tired, reeling and without three injured defensemen.
The Maple Leafs, after falling behind 1–0 in the first period, struck back with two goals from Cody Franson. Phil Kessel and Nazem Kadri later scored to up Toronto’s lead to 4–1 with less than 11 minutes left in the third. As the crowd at Boston’s TD Garden started heading for the exits, thousands of fans in Maple Leaf Square outside Toronto’s Air Canada Centre were watching on a big screen with growing excitement.
Then it all went horribly wrong.
The Bruins, who had won the Cup two years earlier, dug deep and refused to go quietly. After Nathan Horton scored with 10:18 to go to make it 4–2, Boston seemed reenergized while the scrambling Leafs appeared desperate. Matt Frattin almost made it to 5–2 but missed on a breakaway with four minutes left. Only 82 ticks remained when the Bruins pulled goalie Tuukka Rask and scored again as Milan Lucic potted a rebound. Time crept by at a nightmarishly slow pace and Toronto’s 4–3 advantage lasted a little more than 30 seconds. With Rask again off, Patrice Bergeron’s shot from the blue line found its way past Toronto goalie James Reimer at 19:09. Game tied. TD Garden had gone from funeral parlor to madhouse while up in Maple Leaf Square dread seized the Toronto faithful.
The gassed Leafs tried to recover during the intermission before the overtime period, but six minutes into the extra session they found themselves hemmed in their own end by Boston’s attack, the puck loose in front of the Toronto net. Forward Mikhail Grabovski and defenseman Jake Gardiner made futile attempts to clear the zone. Suddenly, Bergeron scored, leaving Reimer sprawled face down on the ice. The Leafs and their fans, some of whom were in tears, tried to grasp the ugly reality. No team had ever lost a Game 7 after leading by three or more goals in the third period.
“There’s no feeling, no way to describe it, I don’t think,” Reimer said in the devastated silence of Toronto’s dressing room.
“I’ve waited half my life for this game, nine years, for this game, and they blew it, in Game 7,” Maple Leafs fan Jake Roulston, 18, told The Canadian Press. “I mean, that hurts.” — John Rolfe
• St. Louis Blues: May 16, 1996; Western Conference Semifinals Game 7—Red Wings 1, Blues 0 (2 OT)
A team that’s closing in on 50 years without a Stanley Cup has taken more than its share of gut punches through the years, staring with Bobby Orr’s notorious posterizing of Glenn Hall and Noel Picard in Game 4 of the 1970 Stanley Cup Final. Of course the Blues were heavy underdogs in that series, but what about when Owen Nolan’s clap bomb from center ice baffled Roman Turek in Game 7 of the 2000 Western quarterfinals? That one really stung because St. Louis entered the playoffs as the top seed against a toothless Sharks team that was described by San Francisco Chronicle writer Tony Cooper as a bunch of “stiffs who should be doing yard work by now.”
But the loss that Blues fans will never be able to shake was Game 7 of the 1996 Western Conference semis. St. Louis was loaded that season with Wayne Gretzky and Brett Hull up front, and Al MacInnis and Chris Pronger manning the blue line, but they’d nevertheless finished 51 points behind a very salty Detroit team. The Blues gave a good account of themselves in the series, winning three straight after dropping the first two on the road. But the Wings won Game 6 in St. Louis, setting up a decisive meeting at Joe Louis Arena.
The two teams swapped chances through a scoreless regulation before the Blues took charge in the first OT. “We had them on the ropes,” St. Louis coach Mike Keenan said after his team outshot Detroit 8–6 in the first extra period.
The Blues’ failure to take advantage of those opportunities is what cost them.
St. Louis goalie Jon Casey made a terrific in-close stop on Sergei Fedorov 14 seconds into the second OT, but it was the last save he’d make. Moments later, the Red Wings’ Steve Yzerman retrieved a puck that bounced off Gretzky’s stick in the neutral zone and raced down the right boards. As he stepped over the blue line he rifled a long distance slapper that sailed over Casey’s shoulder, giving Detroit a 1–0 victory.
“This was my ninth Game 7,” Keenan groaned after the game. “I've seen a lot of heartache, but this one ...” — Allan Muir
• Calgary Flames: June 5, 2004; Stanley Cup Final Game 6—Lightning 3, Flames 2
So close, yet so far pretty much sums up the Flames’ most bitter defeat. After Oleg Saprykin scored the overtime winner for Calgary in Game 5 of the 2004 Stanley Cup Final in Tampa Bay, the Flames headed home needing just one win to secure the franchise’s second championship, and first since 1989. Alas, winning the chalice at home was not to be.
Calgary and the Lightning traded goals in the second period and entered the third tied 2–2. They would remain tied until the second overtime, thanks to cruel fate. Midway through the third period, Flames forward Martin Gelinas, who scored series-winning goals in each of the first three rounds, appeared to score the Cup-clincher. As he charged to the net, the puck ricocheted off his skate and came to rest against Lightning goalie Nikolai Khabibulin’s right skate, which appeared to be over the goal line. The red light did not go on, but the play was given a closer look by off-ice officials who declined to rule in Calgary’s favor.
“We reviewed a number of camera angles and only one showed the puck,” said NHL hockey operations director Colin Campbell. “Based on the angle of the image and the fact that the puck was in the air and on edge, there was insufficient evidence that the puck conclusively crossed the goal line.”
Flames fans were left to wonder What if? Shortly after the puck dropped to start the second overtime, Martin St. Louis—who played for Calgary from 1998 to 2000—scored on a failed clear. The series then returned to Tampa where the Lightning went on to win Game 7 2–1 on the strength of two goals from unlikely hero Ruslan Fedetenko. Having come within inches of a Cup in front of their rabid home fans has grown more painful for the Flames through the years as they have gone beyond the first round of playoffs only once since 2004. — Jeremy Fuchs