The Leafs lost in the playoffs. Again. Six times, in fact.
That’s progress, in a sense – the most playoff games they’ve lost in one postseason during the Brendan Shanahan era. That’s the reward you get for winning a round. More losing, what fun.
If you’re counting, and I am, that makes it 29 postseason games that the Leafs have lost since their first appearance of the Shanahan/Matthews era in 2017, a span that covers the Capitals, Bruins (twice), Blue Jackets, Canadiens, 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 for a ranking. Let’s do that.
But first, a caveat: I very much get that some Leaf fans will want no part of this exercise. I gave it a few extra days to let you work through the grieving process on this latest exit, but that’s going to be nowhere near enough for some of you. If you want to exit out of this article like this guy, I totally get it.
But we all process tough times in different ways, and some of us like to talk our way through them with our miserable fellow travellers. If that’s you, come and join our little support circle as we count down every Maple Leafs playoff loss of this era, from least to most painful.
29: 2017, Round 1, Game 1: Capitals 3, Maple Leafs 2 (OT)
The very first playoff game of the Shanahan era was also the first loss. But it was close, and that felt like a victory against a heavily favored Caps team that had just won the Presidents’ Trophy. Sure, the winning goal was a little bit weak, and of course it had to be Tom Wilson who scored. But just getting to overtime against a team that was supposed to be unbeatable was a win in its own way.
https://www.youtube.com/watch?v=V5bX5-p7xYM
The playoffs are fun! They’re fun, right?
28: 2023, Round 2, Game 1: Panthers 4, Leafs 2
Ah, it feels like it was only weeks ago, doesn’t it? We were all so young back then. We were also still a little hungover from finally seeing the team win a round, so this one couldn’t hurt all that much. Even though they lost, the Leafs played reasonably well, so the outlook for the rest of the series still looked bright. Besides, it was funny to see Paul Maurice holding up his fingers, as if one gesture could suddenly convince all the refs to call prison rules for the rest of the series.
27: 2018, Round 1, Game 4: Bruins 3, Maple Leafs 1
I’ll be honest, I have zero recollection of this game. (Checks box score.) Oh hey cool, Tomas Plekanec was a Leaf for a bit. He scored in this one, which saw the Leafs play reasonably well but run into a strong Tuukka Rask game. Man, why can’t we ever draft a goalie like that.
26: 2021, Round 1, Game 1: Canadiens 2, Maple Leafs 1
This was an awful game, but not because of the loss. Instead, it will best be remembered for the devastating John Tavares injury that took him out of the series. The heavily favored Leafs went on to lose a dull game, but that barely mattered, and if anything it felt understandable given that they'd just seen their leader carried off the ice. Once word came down that Tavares would be OK for the long-term, we all settled back in to watch the Leafs bulldoze the inferior Habs. Which they did. For three games.
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