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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.

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

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

via mapleleafs.nhl.com

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

via davepolaski.blogspot.com

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.

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

via thestar.blogs.com

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

via torontosun.com

10 10. May 8th, 2000 - Six Shots Too little

via ljworld.com

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

via twitter.com

8 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.

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

via youtube.com

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.

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

Steve Mitchell-USA TODAY Sports

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.

5 5. May 4th, 2004 - The Curse of JR 

via drought67.com

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

via thestar.com

3 3. May 28th, 2002 - Hurricane Heartbreak

via youtube.com

2 2. May 13th, 2013 - Bedlam In Beantown

via youtube.com

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.

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

via onthisdayinsports.blogspot.com

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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15 Most Heartbreaking Moments For Maple Leafs Fans Since 1967