The Leafs lost in the playoffs. Once again. Actually six times.
That’s progression in a way — the most playoff games they’ve lost in a postseason during the Brendan Shanahan era. This is the reward you get for winning a round. Losing more, what fun.
If you’re counting, and I am, that’s 29 postseason games the Leafs have lost since their first appearance in the Shanahan/Auston Matthews era in 2017, a length of time that the Capitals, Bruins (twice), Blue Jackets and Canadiens includes , Lightning (twice) and Panthers. Of course, not all losses are created equal. Some are significantly more painful than others.
Hey, that sounds like an excuse to rank. Let’s do that.
But first a caveat: I understand very well that some Leaf fans do not want to participate in this exercise. I’ve given you a few extra days to work through the grieving process of this recent departure, but for some of you that won’t be nearly enough. If, like this guy, you want to opt out of this article, I completely understand.
But we all process difficult times in different ways, and some of us like to talk about it with our miserable fellow travelers. If that’s you, come and join our small circle of supporters as we count down every Maple Leafs playoff loss of the era, from the least to the most painful.
The very first playoff game of the Shanahan era was also the first loss. But it was close, and that felt like a win against a heavily favored Caps team who had just won the Presidents’ Trophy. Sure, the winning goal was a bit weak and of course it had to be Tom Wilson who scored. But just going into extra time against a team that shouldn’t have been beaten was a win in its own right.
The playoffs are fun! They’re fun, aren’t they?
Ah, it feels like it’s only been weeks, doesn’t it? We were all so young then. We were also still a bit hungover from finally seeing the team win a round, so that couldn’t hurt too much. Despite losing, the Leafs played reasonably well so the outlook for the rest of the series was still rosy. Also, it was funny to see Paul Maurice hold up his fingers as if a gesture could suddenly convince all the judges to call out prison rules for the rest of the series.
I’ll be honest, I have no memory of this game. (Checks the box result.) Oh hey cool, Tomas Plekanec was a Leaf for a while. He scored one goal in that game, which allowed the Leafs to play reasonably well, but met a strong game from Tuukka Rask. Man, why can’t we ever sign a goalie like that?
It was a terrible game, but not because of the loss. Instead, what will be remembered most is John Tavares’ devastating injury, which eliminated him from the series. The heavily favored Leafs then lost a boring game, but that hardly mattered and considering they’d only just seen their leader carried off the ice it felt rather understandable. When word got out that Tavares would be fine in the long run, we all settled back in and watched the Leafs level the losing Habs. Which they did. For three games.
Fun fact: This was the only game in the entire series that didn’t go into overtime. The Leafs fell 4-1 down early on and then nearly fought their way back. Also, the Maple Leafs’ final goal was Tyler Bozak by Mitch Marner and William Nylander, giving it a real “The Eiffel Tower was completed the same year Nintendo was founded” vibe.
Man, the 2020 playoffs were weird. So weird that some of you might even dismiss the idea of this series counting as playoffs. The NHL has never really found an answer to that, but the consensus seems to be that it counts, at least when trying to make Leaf fans feel guilty. Anyway, that opener was a boring drudgery in an empty arena, with only one goal going past a goalkeeper.
That was strange. The Leafs went into the series with a 2-1 lead and were on home ice so it felt like a missed opportunity. But they had shown character, fighting to equalize from a 2-0 deficit and then coming back to 5-4 from a 5-2 deficit in the middle of the third half. It was also Matthews’ first multiple-goal playoff game, and even when the series returned to Boston in a draw, there was still room for optimism.
The 2018 playoffs marked the first time the Leafs weren’t overwhelming underdogs, but nonetheless they were tough against a 112-point Bruins team. Losing the opening game in Boston wasn’t too devastating, although the 5-1 final was demoralizing and Nazem Kadri was suspended by a stupid punch.
Well, as long as he learns from it, they’ll be fine.
The Capitals regained the lead in the series in another overtime game, which ended with Justin “Mr. Game 7” Williams. Gosh, I really miss the excitement of Game 7, you said to yourself as a monkey paw curled up somewhere.
If you had a nickel for every 7-3 loss on this list, you’d have three nickels, which isn’t much, but it’s weird that it happened three times. It’s fun to use the word “three times”. It’s less fun to see a team leave Boston 2-0 down and concede a dozen goals. If only there was a defensive-minded $50 million coach who could have prevented this. Ah great.
This was a disappointing loss, especially after the Leafs clinched a Game 1 win and had a chance to go home 2-0. After a half-hearted attempt, it wasn’t to be, and the low point was Kadri going off track again. We didn’t know it then, but it would be his last game as a Maple Leaf.
The Leafs had completely dominated Game 1, so it was important that they immediately dismissed any notions that anything could ever get easy. The score was flattering here; The Lightning led 5-1 until the Leafs scored two late goals.
The first elimination game to make our list, and it’s no surprise that it’s from 2017. The Leafs team was a brave underdog, and the series at least had the good sense of not going to game seven. It hurt a little more that it ended in overtime, but only a little.
Brighter days are upon us, we all thought, like the dumb, dumb little gits we are.
The Leafs came out confidently in this game and led 2-0 after just a few minutes. But a horrible minute early in the second minute sealed their fate, reminding us all that this team can never play the full 60 points and leaving everyone wondering if we had waited 19 years to return in Round 2, only to be overwhelmed by a wild card.
After bouncing back with a solid win in Game 2, the Leafs took a 3-0 lead in that game and seemed to have found their groove against a spirited but overwhelmed Blue Jackets team. Instead, they slowed down and let Columbus climb all the way to the back, sending the game into overtime where Pierre-Luc Dubois scored the winner.
Wait, we’ve got a playful three-goal lead and we’re still only halfway through this list? The whole thing was a bad idea.
This is the first loss in Game 7 of our list. (Spoiler alert: not the last!) He ranks worst because he was relatively early in the era and didn’t have any lost leads or particularly controversial moments. Just a very good Bruins team that would end up going into the finals against a Leafs team that wasn’t quite there yet. At least we can thank Patrice Bergeron’s last-second goal from no empty goal for sparing us all a summer of It Was 4-1 jokes.
Under normal circumstances and for a normal team, it wouldn’t have been so bad. You have a 3-1 lead and would like to finish the game at home, but you lose Game 5 to a strong opponent and have two more chances to finish him off. But this is the Leafs, and it was the seventh year of playoff misery, so for the next two days, everyone had that here we go again feeling.
In hindsight, that was the beginning of the collapse. It was weird to process back then. With a chance to bring the series to the ice against an inferior opponent and enjoy a few days off to rest for Winnipeg, the Leafs were completely unremarkable in the first half, falling 3-0. Then they did the Leafs thing, where they threw a switch late and used two goals from Jake Muzzin (!) in the third period to get into overtime. With all the momentum and free pass going into the second round, it was only a few seconds into overtime before someone managed to:
At that time it was assumed that there were two more swings. In hindsight… yes.
To this day, you feel like this game could have changed the story before it even began. The Leafs had never fallen behind and in Game 5 in Boston they managed to claim an impressive 2-1 win. Now they had the chance to end the game on home ice. Morgan Rielly scored after 10 minutes and the building rocked. But two penalties resulted in two power-play goals for the Bruins, and the Leafs never fully recovered. There was another Game 7 coming up in Boston and we all felt like we knew how it was going to end. We were right.
That might be too low considering it was an elimination-chance game that the Leafs lost in overtime, especially when they led early in the third period and conceded the equalizer on a power play that caused by two phantom highstick calls (and accompanying Oscar-worthy headshots). It just feels like at that point everyone assumed each Leaf series would last seven games, so the response to that loss was less about the missed opportunity and more about the inevitability of it all.
Well, at least the hockey gods didn’t make us work long overtime before we butchered ourselves:
By the way I’ve seen that goal quite a few times and this is the first time I’ve noticed our old pal Bryan McCabe in the bottom corner as the Panthers managers celebrate. Do you think he’s mad that Jake showed up in Toronto and stole his “What’s McCabe even doing in this play?” Chic?
With the Leafs leading 2-1 and having a chance to put the Lightning on the gas, that was Sunday night’s disappointment Only the smartest people saw it coming. A strong Game 3 followed and was another example of this team stepping on the gas once things are going well.
How do you haunt a comeback where you saved three goals in the last five minutes of regular time before winning in overtime? If you’re with the Maple Leafs, the answer is a total no-show, where you fall behind early and then watch a career backup named Joonas Korpisalo parry whatever your overpriced attack throws at him.
That loss meant more than just the end of the streak—it was the turning point that left everyone with a sinking feeling that there might be something fundamentally wrong with this team.
A year. That’s how long it had been since the Leafs lost to the Lightning in 2022, sparking another reminder that nothing this team did in the regular season would ever matter and it was all about the playoffs. They struggled through a meaningless season, finally came back to reality, against the same opponent, and then… they got completely slapped in the face. Didn’t even show up. It was inexcusable and people were very angry at the time. About a week later, not so much.
It was a brutal game that was even more painful than the one-sided result suggests. After the Leafs pulled off a powerful win on home ice and the ghosts of 2013 sought revenge, the two teams engaged in a wild first period that ended with Boston leading 3-2. The Leafs fought back in the second, scoring two goals and taking the lead in the third. It was at this point that everything fell apart as the lead lasted just a minute and a certain poor playoff Freddie scored the winner. It all left Leaf fans feeling like they were in love with Lucy’s football once again.
In hindsight, isn’t it a bit amazing that that very game – the poor start, comeback, controversial no-goal and crushing loss in overtime – was played in Game 5 instead of Game 7? It was a crushing loss, but it would have been far worse if the Leafs had come back from a 3-0 series deficit and then lost the deciding game. I think so now. This team broke my brain.
If you listened closely, you could hear a million different takes screaming “This time feels different” at the same time. Once again, the Leafs saved one of their least inspiring attempts until the end, managing just one goal (by a defender) from 31 shots.
Well, two goals if you count the one they scored from a pick play. Which literally every other umpire in the history of this league would count, not that I’m still bitter or anything.
The good news is that they were shown more respect in the handshake line, so I can’t rate this one any worse.
I don’t think anyone will object to the Habs being at the top of the list. The surprise might be that I gave first place to Game 6 and not the crucial Game 7. I could totally imagine flipping them making sense. But man, it felt like it was over after Game 6, right? By the time Game 7 came out, many of us had already published our autopsies. We just had to watch the most promising season we had ever seen unfold. Which also happened to be a deadly boring no-show in front of a few hundred fans. A Nylander goal with two minutes left averted a shutout loss that would have been the fate they deserved. There wasn’t a point in the game where you thought these guys would pull through.
Contrast that with Game 6. The Leafs had dominated the series after the injury game against Tavares but let their opponents off the mat in Game 5. If ever there was a time for a killer instinct, this was it. What’s more, it would be the first time the Leafs have played in front of real fans in over a year. They came out flying. They had to.
And then they didn’t. If anything, this might have been their worst start to the series, as the Leafs’ biggest stars seemed to take hopeless shots at Carey Price for a couple of spells. Midway through the third period, the Canadiens took a 2-0 lead, after which the Leafs made their characteristic comeback. That put them into overtime, but a loss of possession from Travis Dermott and a routine save from Jack Campbell failed to end the game.
This also ended the series, although it only became official for another game. If you want to put Game 7’s funeral procession first, then go ahead. But for me that was the low point.
(Photo: Dan Hamilton / USA Today)