Like something that happens every 50+ years or so and is so obscure most fans don’t even know it’s possible and that (gets absolutely buried in “Leafs win the Cup” replies)
Accidental own goal with your goalie pulled for a delayed penalty? (Wisconsin women’s hockey team had that on a missed pass a few years ago. Team came to the bench and asked Mark Johnson, “wait, does that count?” Oops.)
Think this has happened five times: Reigning Cup champ not making it to the playoffs next season. Incidentally, the '67 winners were the first to do it.
Ooh, better answer: Losing the overtime "charity point" if you pull your goalie in OT and get scored on with an empty net. I'm not even sure if that's ever actually happened.
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Bonus - it is was Ryan O'Reilly's only penalty of the season in game #72 (3/29/14) & he kicked the puck not knowing his stick was broken...
https://youtu.be/aVzBcLWo4Kg?si=O5FvCZZMWURhmciq