Ranking the Maple Leafs' most heartbreaking series-clinching losses

The Toronto Maple Leafs are victims of expectations and, especially the last half-decade, all they've known is misery in the playoffs.

Whether it was a quick goal in overtime or a slower, full-hour death march, the Leafs have been knocked out of the postseason in a plethora of painful ways in recent memory. The club has done this so much to its tortured fan base that it currently holds the second-longest streak of losses in series-clinching games at nine.

With that in mind, it only makes sense to rank each of these L's by how heartbreakingly devastating they were to Leafs fans, naturally.

9) May 27, 2021 — 4-3 (OT) loss in Game 5 to Montreal

With their first playoff series win in 17 years just an hour of play away, the Leafs washed away their momentum as the Canadiens came out of the gate with a 3-0 lead through the first 25 minutes.

For a normal team, letting the game fizz out to a loss in regulation would suffice, but this is a squad that just has to be dramatic. Without allowing another goal in regulation, Toronto worked itself back and eventually forced overtime. It was there that a misplay caused a 2-on-0 breakaway that led to Nick Suzuki scoring the winning goal just 59 seconds after the puck was dropped.

A whole new way for the Leafs to lose hold of a playoff series and the loss that kickstarted Montreal’s comeback and forced Game 7.

8) Aug. 9, 2020 — 3-0 loss in Game 5 to Columbus

In the middle of the postseason bubble, the Leafs were seen as the easy favourites to move on against a Blue Jackets team that was experiencing their first season since Artemi Panarin left for New York. Despite outshooting Columbus 33-22, the Leafs were kicked out before the real 2020 postseason even began by the hands of opposing netminder Joonas Korpisalo in the qualifying round.

Despite it being frustrating, with the context of being in the middle of a pandemic and forcing GM Kyle Dubas to make a few defensive upgrades to kickstart their current campaign, it wasn’t all that bad compared to other recent gut punches.

7) April 21, 2019 — 4-2 loss in Game 6 to Boston

Up 3-2 in a first-round playoff series during a postseason they seemed destined to go deep into, The Maple Leafs just let it slip away.

It was in front of their home fans in Game 6, but the Leafs came out flat-footed and were outplayed through the full hour of action. That night wasn’t one of their most deserved wins, but the Bruins were simply the better team and managed to extend that series en route to a Stanley Cup final appearance.

6) May 29, 2021 — 3-2 (OT) loss in Game 6 to Montreal

In a similar vein, it wasn’t the heartbreak of being kicked out of the playoffs, but instead the agony of extending a series that they should have ended immediately. With fans back in the building, Montreal was able to control the narrative right up until the final handful of minutes.

The Leafs battled back from a two-goal deficit to force an overtime period where they were completely in control, only to have Jesperi Kotkaniemi score on Montreal’s second overtime shot.

5) April 25, 2018 — 7-4 loss in Game 7 to Boston

The Leafs had the momentum going their way in this first round matchup in 2018. They forced a seventh game after going down 3-1 in the series, but having gone through the same sequence of events just five years prior, we all knew what the outcome would be. Even with the Big Four up front, the result was still the same.

The game unraveled for Toronto in the third period. With a 4-3 lead heading into the final frame, the Leafs were thrown off quickly by two Bruins goals in the first six minutes. Now with the lead, Boston kept the pressure on before David Pastrnak sealed the series with the insurance marker.

4) April 23, 2019 — 5-1 loss in Game 7 to Boston

After losing Game 6 and being pushed into this do-or-die match, momentum carried the Bruins to victory in the end. A fairly even game played through the hour of action, but with every Boston shot the TD Garden became more and more of a pressure cooker.

This loss was the final nail in the coffin of Nazem Kadri’s time in Toronto, as the series slipped away and a lot of fingers were pointed at his suspension that kept him off the ice for the last five games.

If anything, this loss was the signifier that the Bruins are just able to overcome anything the Leafs throw at them. Four consecutive series-clinching losses are dedicated just to that team.

3) May 4, 2004 — 3-2 (OT) loss in Game 6 to Philadelphia

It wasn’t clear at the time, but a Jeremy Roenick shot sent the Leafs out of the playoffs for almost a decade. A second-round matchup after the Leafs sent the Ottawa Senators out of the postseason yet again, the battle against the Flyers was quickly bouncing around as Toronto came back from a 2-0 series deficit to even it up and make it interesting.

Despite winning Game 3 and Game 4, the Leafs lost the two final playoff games the city would see in a very long time and the last of Mats Sundin’s era in Toronto. That team was full of eventual Hall-of-Fame players to go with Sundin: Brian Leetch, Ed Belfour, Joe Nieuwendyk. Even top-tier players like Tomas Kaberle and Alexander Mogilny couldn’t send the Leafs past the Flyers.

It is a heartbreaking sight to see those names never get a chance to go on a deep run wearing the blue and white, and it was all Leafs fans had to hold on to until they were up 4-1 in the third period against the Boston Bruins in 2013.

2) May 13, 2013 — 5-4 (OT) loss in Game 7 to Boston

A game remembered by the phrase “it was 4-1” has haunted every single fan of this team through the modern era of playoff losses. The team made its first playoff appearance since 2004, led by Phil Kessel and a rag-tag group of players that were able to comeback from a 3-1 series deficit and build that momentum all the way to a three-goal lead with 10 minutes and 42 seconds left in regulation.

One of hockey’s greatest unravelings happened next as Boston and its stars put everything they had on goaltender James Reimer and eventually forced overtime with an equalizing goal with just seconds left on the clock. With the wind behind their backs, Patrice Bergeron sent heartache through Toronto just over six minutes into overtime and the franchise went into a panic.

Almost everything — including the logo — from that era is gone from the organization. A rebuild that included getting Auston Matthews at the top of the 2016 draft has sent them into sky-high expectation territory, for them to only still be losing series-clinching games.

1) May 31, 2021 — 3-1 loss in Game 7 to Montreal

Recency bias aside, what went down Monday night in Game 7 versus Montreal has to be the cherry on top of the most painful Maple Leafs playoff disappointment to date.

Finishing 11 wins and 18 standings points clear of the fourth-place Canadiens in the regular season, the top-seeded team in the North was picked by essentially every pundit on earth to advance over the Habs (quite easily in many cases) and had a 3-1 series lead after four games.

To drop three straight close contests to a lower-seeded squad — including two in their home building —when everything was trending their way is an excruciating way to go out, and the pain the team and its fanbase feels is only multiplied by the fact that this division, during this season, provided the "easiest" path Toronto will have to a Stanley Cup final berth, as it's back to hanging out with the Lightning, Bruins, Panthers and Co. in the Atlantic Division next year.

Pain. So much pain.

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