Top 10 Most Heartbreaking Losses in Toronto Maple Leafs History

As a Toronto Maple Leafs fan residing in Montreal, I can assure you that life is never easy. If I want to avoid bar room brawls, my jersey can only be worn in my living room; beautiful Quebecois women will turn and walk away at the mere mention of the blue and white; and I’ve heard the number 1967 far more times than I care to admit.

Even when the Leafs’ aren’t involved, their fans can have their hearts broken. Who can forget Easter Sunday in 2007? The Islanders beat the Brodeur-less Devils in a shootout to secure the final playoff spot after the Leafs had vanquished the Habs the night before with an epic 6-5 win to momentarily jump into eighth place. I can assure you my grandparents will never forget the cursing coming from our basement. That Easter evening pales in comparison to the Leafs’ most recent playoff fiasco in Boston in 2013, a game that my own grandkids will surely curse themselves one day. Or who could forget Kerry Fraser’s blown call on Gretzky in 1993? 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. If you think that’s bad, just wait until you read about Kerry’s father. (Spoiler alert: it involves an axe and a mobile home.)

Alas, while I must list these top 10 heartbreaking losses, I await the day when Lord Stanley’s Cup travels its rightful path down Yonge Street and I can start to yell out ‘93 in Montreal, instead of hearing chants of ‘67. It may not help me with the local women, but if the cup does ever return home, I (along with the rest of Leafs Nation’s ex-pats) may just have to move back with it.

This column is dedicated to the memory of legendary Leafs’ coach Pat Quinn. His passing is a truly heartbreaking loss for the entire hockey world.

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12  10. Can’t Win without Quinn (Carolina, 2002)

Our list begins with the Leafs’ Game 6 overtime loss to Carolina, who had been without the hospitalized Quinn for part of the series. The Leafs trailed the series 3-2 and were down 1-0 with less than a minute remaining in regulation. It was no surprise that captain Mats Sundin stepped up after having returned from injury, scoring in a scramble around the net with just 21.8 seconds remaining.

Of course, this being the Leafs, it was all for naught and the ACC would fall silent as Carolina went on to win the game and the series after an overtime winner from Martin Gelinas. (Interesting side note: this is the lowest scoring six-game series in NHL history with a meager total of just 16 goals scored.)

11 Six Shots (New Jersey, 2000)

Steve Russell/Toronto Star

You would think that when facing elimination in the Stanley Cup Playoffs, an NHL team would be able to muster more shots than my Peewee AAA team. But, then again, this is the Toronto Maple Leafs we’re discussing. Facing elimination at the hands of the Devils, the Leafs found themselves down 1-0 a mere 18 seconds into the game and from there managed three shots in the first; two in the second and, with 20 minutes left to save their season, they managed one... One shot, in the third period.

Fittingly for this absolutely abysmal affair and one of the most embarrassing moments in Leafs history, it was the lowest recorded shot total for an NHL team since... You guessed it, 1967.

10 Leafs Lose their Ace (Boston, 1933)

via jim-sands.ca

Though it wasn’t a loss on the score sheet, one of the most heartbreaking Leafs losses occurred on December 12th, 1933, when the Bruins’ Eddie Shore smashed into the Leafs’ star forward Ace Bailey. Ace collapsed onto the ice, cracked open his head and never returned to the ice again after the near-fatal incident.

Leafs enforcer Red Horner, the NHL penalty minutes leader, retaliated by knocking Shore out with a single punch; though that paled in comparison to the reaction of Bailey’s father, who had to be restrained by law enforcement from traveling to Boston with his firearm to see Shore.

Thankfully, Bailey made a full recovery and on Valentine’s Day of 1934 was able to attend a game in his honour between the Leafs and a special team of All-Stars. Love was in the air and all was forgiven as Shore and Bailey embraced before the game to the deafening cheers of Leafs’ Nation.

9 “Like It Always Does” (Philadelphia, 2004)

“It’s a pretty sickening feeling” is how Brian Leetch described the Leafs’ 3-2 overtime loss to Philadelphia in Game 6 of the 2004 Eastern Conference semi-finals. Leetch, who had been brought in at the trade deadline, had left his defence partner Brian McCabe high and dry on the Jeremy Roenick wrister that ended the Leafs’ playoff hopes. Sundin, playing his familiar clutch role, had tied the game up with less than five minutes on the clock, but it was the Flyers who “… were able to put the puck in the net when it mattered most.”

“It’s tough to swallow,” uttered Leafs enforcer Tie Domi, but as Toronto Star columnist Rosie Dimanno so succinctly and cynically wrote at the time, “So it ends, like it always does.”

8 Thieving Fans in the Stands (New York, 1971)

While this loss may not have been the most heartbreaking, it was certainly one of the most bizarre. In 1971, the Leafs’ took on the heavily favoured Rangers and lost in six games, though it was Game 2 that featured the most noticeable loss. In one of the many melees that punctuated the gory series, the Rangers’ Vic Hadfield flung Bernie Parent’s goalie mask into the waiting arms of the New York faithful. Leafs executive King Clancy waded into the antagonistic crowd and valiantly attempted to retrieve the mask, but in a mark of true NYC hospitality, one lucky fan kept it as a souvenir.

7 Howe’s Revenge (Detroit, 1950)

via puckstruck.com

One of the bloodiest series in Leafs’ history may have gone to seven games, but it was really over after Game 1, the moment Gordie Howe went down in a near-fatal collision. With the underdog Leafs up 5-0 in the first game, Howe took a run at the injured Ted Kennedy, who pulled up at the last second and caused Howe to tumble head-first into the boards. Believing that Kennedy had deliberately intended to injure their star forward, Detroit was out for blood and the rest of the series saw the ferocious Wings pound the tentative Leafs into submission. The final game was a scoreless draw until Wings’ defenceman Leo Reise scored a fluke, overtime winner.


5 Ode to the Garden (Buffalo, 1999)

In February of 1999, the Leafs played their final game at Maple Leaf Gardens, moving to their current home at the Air Canada Centre. The Leafs hoped to christen their new home with a trip to their first Stanley Cup Final in 32 years.

That May, Toronto would make a long playoff run, meeting the Sabres for the first head-to-head matchup in their playoff history, eventually losing in a short five games. Despite the dominant Dominik Hasek missing the first two games in Toronto, Buffalo was able to get the split and never looked back, scoring 14 goals over the next three games. The seventh seeded Sabres advanced to the Stanley Cup Final, while the Leafs lost in the conference final for a third time in the 90's.

The Garden, like the Leafs’ Cup hopes, would lay dormant for the next 15 years.

4 Murphy’s Law (St. Louis, 2000)


Your team is up 5-0 with 15 minutes to play. What could go wrong? Maybe someone on your bench uttered the word “shutout”, but that would only mean one or two goals, right? Then you remember you’re a Leafs’ fan and that, what can go wrong, will go wrong. In the time it takes some of us to shower, the Leafs got hosed, blowing a five-goal lead to the St. Louis Blues, giving up six unanswered and losing in overtime.

Leafs netminder Curtis Joseph called it “the strangest game that I’ve been a part of,” while Leafs’ coach Pat Quinn admitted he didn’t know “how the hell this happened.”

2 The Great One (1993)

It was early in the morning on May 28th, 1993 and the late Hilton Fraser had gone to bed after watching his son Kerry miss one of most important calls of his career, allowing the Great Gretzky to get away with a high stick on Doug Gilmour in overtime and, minutes later, buried the Game 6 winner.

One irate Leafs fan drove to Sarnia and began breaking 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, 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.”

We forgive you, Kerry, but only because we’re still scared of your father.

1 Meltdown in Beantown (Boston, 2013)

The Leafs gave it everything they had for over 400 minutes of intense playoff hockey, and then the wheels fell off in the home stretch, with the finish line in sight.

As Tuukka Rask so eloquently stated about Game 7 overtime, “It’s do or die. Either you’re a hero or an a**hole.” Not that Leafs fans needed any confirmation of this, but, according to the Elias Sports Bureau, Toronto’s loss in Boston was the worst Game 7 collapse in NHL history.

“We had a chance to win this series, and we gave it away,” said Cody Franson.

After the game, netminder James Reimer described the crushing void, saying, “[After] tonight… there is no next time. There’s just next year, and really, it’s just an empty feeling."

That’s right, Leafs Nation, there’s always next year.

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