It was a simpler time, back before we’d been through multiple overtimes and when we still assumed the Capitals would roll past the Leafs easily. We didn’t even know who Dart Guy was. Look at us back then, we were so young.
Well, fair’s fair, so today we’ll visit the other end of the spectrum, with a ranking of the 10 worst Leafs playoff games of the last three decades.
There’s one important note to keep in mind, though. Ranking a team’s best games is a relatively straightforward exercise. Most playoff runs end in misery eventually, so you just take the games that you enjoyed most as a fan at the time, and there’s your list – with few exceptions, the best games generally hold up well.
But bad games are a little bit trickier, since sometimes you don't know just how miserable a game will make you feel down the line. An especially tough playoff loss is like a slow-acting poison, and you don't feel its full effects until years later. Hindsight is going to play a big role today, especially as we get near the top of the list.
But let's start our countdown a little more than 27 years ago, from a spot just outside the Maple Leafs' blue line.
No. 10: 1990 Norris Division semi-finals, game three: Blues 6, Maple Leafs 5 (OT)
The 1989–90 Leafs team was their best in a decade. That's not an especially high bar, and the team still only finished .500, but they ranked third in the league in goals scored and seemed as if they might finally be building something resembling a winner.
But after dropping a pair of 4–2 decisions in St. Louis, the Leafs headed back to Toronto facing a must-win in game three. They fell behind 5–3 in the third, but fought back to force overtime with two late goals that had the Gardens crowd roaring. An overtime win could have been the sort of clutch comeback that turns a series.
Instead, Sergio Momesso went five-hole on Allan Bester from outside the blue line.
The Blues closed it out in five games, the 1990–91 season turned out to be one of the worst in team history, and the Leafs wouldn't make it back to the playoffs until 1993. Momesso later played for the Leafs, but nobody ever forgave him for this goal.
No. 9: 1999 Eastern Conference final, game one: Sabres 5, Maple Leafs 4
The Leafs' 1998–99 season had already included a 28-point improvement, the first playoff appearance in three years, two series wins, and one Markov salute. Now they headed to the conference final with momentum, home ice and a winnable matchup against the seventh-seeded Sabres.
There was just one problem, and it was the same problem every Sabres opponent faced in those days: the best goaltender in the world. Dominik Hasek had just won back-to-back Hart Trophies, not to mention single-handedly winning Olympic gold. At that point, he was the scariest player in hockey.
And then, hours before game one, a playoff miracle (for Leafs' fans, anyway): Hasek was hurt, and the Leafs would be facing backup Dwayne Roloson instead. It was the perfect opportunity to jump out to an easy lead in the series.
And sure enough, Roloson struggled, allowing four goals. But Curtis Joseph gave up five, and the Sabres stole the opener without their best player.
The Leafs took game two, but Hasek returned for game three and shut them down the rest of the way. The Leafs never seemed to recover from the missed opportunity in the opener, and their third conference finals appearance of the decade ended in five games.