15 Most Heartbreaking Moments For Maple Leafs Fans Since 1967

Do you remember where you were the last time the Leafs raised the Stanley Cup? If you do, then chances are you also remember where you were when Neil Armstrong walked on the moon, when Muhammed Ali controversially refused military service and when Pink Floyd released their debut album "The Piper at the Gates of Dawn." If you don't remember, that's okay, you are like most of us. Yes, it has been a long and tiresome 49-years for Toronto Maple Leaf fans, as decades have come and gone, inflated with hope and exhausted by disappointment. In fact, the Leafs have yet to even make it back to the big dance in June and they have watched 24-other teams enter the league since, lessening their chances more and more. The Sittler era, Gilmour era and Sundin era, each came finger-tips away from a Stanley cup final and a chance to end the drought in Toronto.

Last Friday, marked an extremely special moment for the organization, as the Leafs selected potential superstar Auston Matthews first overall at the NHL Entry Draft. The pain and suffering has finally begun to pay off for Leaf fans everywhere. With the Leafs finding themselves in the most promising position since 1967, lets count down the top 15 most heartbreaking moments for Maple Leafs fans since they last won the cup and hopefully put them forever behind us in the process.

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15 November 29th, 2000 - Never Too Late to Lose 

It's pretty tough to experience heartbreak in November of the NHL season, but leave it to the Leafs to dream up the perfect disaster in just 15 minutes. On November 29th, 2000, the Leafs held a 5-0 lead in their own building with just 15 minutes to play in the third period against the St. Louis Blues. The Blues were coming off of a Presidents Trophy the year before and were one of leagues offensive powerhouses. Led by Alexander Khavanov's two third-period goals, plus a goal and an assist from then captain Chris Pronger, the Blues managed to force the game into overtime where they would complete the comeback, winning 6-5 and absolutely stun the crowd at the Air Canada Center in Toronto.

14 February 11th, 2012 - The Habs Say Farewell to Sundin 

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On a night that was supposed to culminate everything that it meant to be a Toronto Maple Leaf, the Leafs failed to show up, resulting in one of the most painful and utterly atrocious performances that many fans can remember watching. Before puck drop, the Leafs celebrated the career of Mats Sundin and concluded the ceremony by raising his banner to the rafters at the Air Canada Center. It was impossible not to be swept away by the emotion and pride encapsulated in that moment and Leafs fans could not wait to watch their team honour Mats on the ice, against their greatest rival - the Montreal Canadiens. The Habs would outplay the Leafs in every facet of the game, silencing the crowd with a 5-0 victory and sending Leafs fans home frustrated and disheartened by the way that they represented their all-time great centerman.

13 April 8th, 2007 - Islanders Clinch, Leafs Go Golfing

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It was the final day of the NHL season and the Leafs had beat the Habs in a thrilling 6-5 contest the night before, putting themselves in a playoff spot and eliminating the Habs in the process. The Islanders needed a win the next afternoon in New Jersey to jump the Leafs for the 8th and final playoff seed in the Eastern conference.

With time running out and the Islanders up a goal, a frantic scramble in front of the Islanders net would result in a John Madden goal at 19:59 of the third period, tying the game and, in the meantime, saving the Leafs season. However, the Islanders would win the shootout and officially send the Leafs packing. In fact, the Islanders had to win their last  four games of the season, including one against the Maple Leafs to qualify for the post-season, and they did it. Heartbreaking.

12 April 22nd, 2003 - Leafs Bullied in Game 7 on Broad Street

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After an incredible Conference Finals playoff run in 2002, Leaf fans everywhere had high expectations for the team once again in 2003. They would meet the Philadelphia Flyers in round one of that playoff and the hockey universe was instantly treated to an exciting and fast-paced series. That was until game seven, when the Leafs fell apart. A gruelling game six saw the Leafs and Flyers duke it out all the way into double-overtime, before Travis Green would play hero in front of the ACC faithful, forcing a game seven. The Leafs would fly back to Philadelphia, but apparently left their sticks, skates and manhood on the flight, as the Flyers would run right through them with a 6-1 shellacking, sending the Leafs home quicker than Lindros got out of Quebec.

11 March 13th, 2003 - Doug Gilmour Returns, Kind of...

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Arguably one of the greatest Maple Leafs of all-time, Doug Gilmour manifests what it means to be a Toronto Maple Leaf. Gilmour served as the Leafs captain from 1994-1997 and brought the Leafs within a game of the Stanley Cup Finals in 1993. Gilmour would leave the Leafs in 1997, but to the delight of the Maple Leaf faithful, would return at the trade deadline in 2003. Gilmour was not going to be able to produce the same way he did 10 years prior, but having him back on the team was an incredibly big deal for the city and the players. On March 13th, 2003, Dougy returned in a game against the Calgary Flames, only to collide with Flames forward Dave Lowry during just his second shift back wearing the blue and white. Gilmour tore his ACL and would announce his retirement a few months later, abruptly ending the much anticipated return and, once again, leaving Leafs fans disappointed and crestfallen.

10 May 8th, 2000 - Six Shots Too little

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After losing game five of the Eastern Conference Semi-finals on home ice, the Leafs were forced to face elimination in New Jersey as they suited up for game six. If we thought the no show in 2003 was bad, this episode of Toronto Maple Leafs' most promising disasters has to take the cake. With their backs against the wall, the Leafs crawled onto the ice and watched the Devils skate around them for 60 full minutes, as they were outshot in the 3-0 loss by a mark of 26 to 6. The Leafs were only able to muster  six shots on goal against the worlds greatest goalie in Martin Brodeur. We're not too sure who drew up the game plan on this night, but it is one of the most embarrassing performances in Leafs history, as they did indeed set the record on that night for least amount of shots in an NHL game. Well done boys, well done.

9 January 20th, 1982 - The End of the Sittler Era 

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Darryl Sittler WAS the Leafs throughout the 1970s. Despite all of the big names on the team, Sittler was the captain and the leader of the franchise. The 1970s saw the Maple Leafs in the playoffs under Sittler's wing in every year but 1973 and saw the franchise getting into the second and third rounds quite consistently. Many believed that Sittler and his team would eventually make it to the promise land and collect another Stanley Cup for the city of Toronto. In the ladder half of the 1970s and early 80s, however, Sittler began to find himself on a different page than the Leafs management team, often resulting in conflict and whispers about Sittler's future with the club. Finally on January 20th, 1982, Sittler was traded to the Philadelphia Flyers and that was it. The Leafs would miss the playoffs that season, ending the eight-year playoff streak that Sittler had built in Toronto. The Leafs would struggle mightily to become relevant again and it wasn't until 1986 that they were back into contending form.

8 1987 Playoffs - It Slowly Slipped Away...

With the debacle of the Sittler era officially behind the club, the Leafs found themselves with a new identity in the likes of Wendel Clark, Rick Vaive and Steve Thomas midway through the 80s. Heading into the 1987 playoffs, the Leafs were underdogs in round one, but ousted the St.Louis Blues in six games for the right to meet Detroit in round two. After going up 2-0 in the series and outscoring the Red Wings 11-4 on their own ice, the Leafs headed back to Toronto in firm control of the series.

The Leafs would lose game three but retaliate with a win in game four, restoring their two-game lead in the series and putting them one win away from their first conference finals in 10 years. It was all downhill from there, however, as the Leafs would only manage to score two goals for the rest of the series, being blanked 3-0 in game five and in the clinching seventh game, ending their season and completing one of the worst collapses in Maple Leaf history.

7 May 24th, 1994 - Canucks "Bure" the Leafs

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This game often falls off the radar in terms of heartbreaking experiences for Leafs fans, so we're here to remind you how much it sucked. Coming off of heartbreak the year before against Los Angeles (we'll get there), the Leafs looked determined to finally break though to the Cup Finals. After dismissing the Chicago Blackhawks and San Jose Sharks in rounds one and two, the Leafs would meet Pavel Bure and the underdog Vancouver Canucks, who finished as the 7th seed in the Western Conference, 13 points back of the Maple Leafs.

The Leafs would win game one and seemed to be right on the right path. However after three straight losses and being shutout in games three and four, the Leafs found themselves with their backs to the wall and very little momentum going into game five. They would, however, bounce out to a quick 3-0 lead in game five and seemed to be in tight control of the play. Sadly, the lead didn't last long, as the Canucks would storm back to tie the game in the second period, ultimately forcing the game into overtime tied at three and setting the stage for heartbreak once again. Greg Adams would score within the first minute of double overtime, sending the Canucks to the Cup Finals and, once again, sending the Leafs home in painful fashion.

6 April 18th, 2015 - The Great One That Got Away

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Since the age of 12, Connor McDavid was the main focus for the majority of NHL scouts, as they knew that one day he would develop into what could potentially be the next "great one." Being born and raised in Newmarket, Ontario, just a half-hour north of Toronto, it was mutual in that Leaf fans wanted McDavid and McDavid wanted the Leaf fans. April 18th, 2015 would mark the day of the draft lottery and a day that changed the future of many franchises for better or for worse. With McDavid being a shoe-in as the #1 pick, everyone knew that the draft lottery meant a revolutionary change for their organization. The Leafs stood in with the fourth best odds in the lottery and a 9.5% chance of landing McDavid. As the lottery came to an end and the Oilers took claim to the number one pick again, most Leaf fans felt let-down but somewhat expected the outcome to go against them. After all, there was technically a 90% chance that we wouldn't land McDavid, so it's not that disappointing, right? Not quite.

A couple of hours later, frustration turned into absolute heartbreak, as it was revealed that after three of the four balls had been drawn, the Leafs actually had the best chance of landing McDavid and simply needed a 2, 7, 8 or 13 to complete one of their combinations and win the lottery, whereas the Oilers needed either a 1 or a 10, giving them just half the chance that the Leafs had at this point of the lottery. The final ball drawn, #1 of course. Oilers land McDavid and Leafs fans are once again left broken and defeated.

5 May 4th, 2004 - The Curse of JR 

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Just one year after the game seven no show in 2003, the Leafs would find themselves in the second round to face the Flyers once again. After some of the more heartbreaking moments in Maple Leafs history from 1999-2003 (again, almost there), the 2004 playoffs felt like it could be the Leafs last chance  at making a deep playoff push, as key contracts for plaeyrs such as Gary Roberts, Joe Nieuwendyk and Alexander Mogilny were set to expire and whispers about the NHL lockout began to float to the surface. Therefore game six against the Flyers was a stinger. With the Leafs down 2-1 late in the third period, captain Mats Sundin was able to once again come to the rescue and tie the game with just five minutes to play, sending it to overtime. Once again however, the Leafs would be on the opposite end of overtime glory as Jeremy Roenick would fly down the wing just under eight minutes into OT and roof one past goaltender Ed Belfour. The Leafs were out and the door was officially closed. The curse of JR would hang over them, as the Leafs wouldn't make the playoffs for another seven seasons.

4 May 31st, 1999 - Goodnight, Maple Leafs Garden

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The 1999 playoffs saw Leafs Nation in a frenzy, as the Leafs had rolled through the Philadelphia Flyers and Pittsburgh Penguins, en route to a visit with the Buffalo Sabers in the Eastern Conference Finals. Having already knocked off the top-seeded Flyers, Leafs fans figured this was finally the year, as the Sabers finished in the 7th seed, six points behind the Leafs. It would be perfect, as the Maple Leafs, in their final season at Maple Leaf Gardens, would get a chance to play in the Stanley Cup Finals and perhaps win it all. Yeah, it would have been, but the Leafs in perfect Leafs fashion would quickly let the series get away as Buffalo would take a 3-1 lead with game five scheduled at the Gardens. It would be the last game ever scheduled at the Gardens, as the Sabers handed the Leafs a 4-2 loss, closing another emotional and sentimental chapter in Maple Leafs history.

3 May 28th, 2002 - Hurricane Heartbreak

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After the aforementioned Conference Finals against the Sabers, the Leafs would find themselves back in the same position in 2002, this time against the Carolina Hurricanes. After stealing game five in Carolina 1-0, the Leafs headed back to Toronto in an effort to push game seven and the chance to play another game, for a trip to the Stanley Cup Finals. With the Leafs down late in the third period once again (broken record alert), Mats Sundin was there to strike, tying the game at 1-1 with just 21 seconds left to play. With the game in overtime and the Leafs just a goal away from forcing game seven, Hurricanes forward Martin Gelinas made his way to the slot, uncovered and was able to slide it past Curtis Joseph, ending the dream in the blink of an eye and, once again, blanketing Leafs Nation in failure and disappointment.

2 May 13th, 2013 - Bedlam In Beantown

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We all remember how this one goes...but lets relive it since we're here, right? In the Leafs defense, they were supposed to have no chance in this series. They had struggled mightily to beat the Bruins over the past two seasons and always seemed to be on the wrong end of a complete tail-spanking whenever these two teams faced off. On top of that, Phil Kessel, the Bruins once prized rookie turned Leafs All-Star, had failed to produce when facing his former team and had been criticized heavily for this among other things.

After being down three games to one in the series, the Leafs were able to rally off back-to-back 2-1 victories in Boston and Toronto respectively. With the Leafs up 2-1 heading into the third period of game seven, they decided to score two more, putting them up 4-1 and setting the stage even more-so for the ultimate playoff collapse. With just 10 minutes left, the Bruins rallied for three goals including two in the final 1:22 of the third period. Patrice Bergeron would tie the game and also score the winner in overtime, completing the 5-4 game seven comeback and officially becoming public enemy number one in Toronto that summer.

1 May 27th, 1993 - Gilmour, Gretzky and the Ghost of the High Stick

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Of all the heartbreak that you have endured throughout this article, nothings tops this one for a few simple reasons. First off, this was the closest that the Leafs have been to the Stanley Cup Finals since 1967 (one game away), Second because the way that they lost was an absolute travesty, Thirdly because Gretzky, of all people, just had to be the one involved as if he hadn't had enough success already.

With the score tied up at four in overtime of game six, the Maple Leafs found themselves on the penalty kill. As Gilmour fled to the point in an attempt to block a shot, Gretzky got his stick up, smacking Gilmour in the face but the play somehow went undetected by referee Kerry Fraser. The whistle was blown but no penalty was called. Gretzky would end the game in overtime on the next play when he should have been in the penalty box all along. The Leafs would never recover and the Kings would win game seven, booking their ticket to the Stanley Cup Finals and stabbing the heart of Maple Leafs nation once again.

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