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.
No. 8: 2003 Eastern Conference quarter-finals, game seven: Flyers 6, Maple Leafs 1
Pat Quinn's pre-lockout Maple Leafs won at least one round in five out of six years. The 2002–03 squad was the exception.
That's not the end of the world; even good teams sometimes get bounced early. But the Leafs certainly didn't look like a good team in game seven in Philadelphia. The series had been a close one, featuring seven periods' worth of overtime. On this night, once the Flyers got going, it wasn't close at all.
Does it hurt more to be eliminated in a blowout, or in a close game? That's a tough one to answer, and the Flyers would kindly provide Leafs fans with a handy comparison point a year later. But we'll get to that one in a bit.
No. 7: 2000 Eastern Conference semi-finals, game six: Devils 3, Maple Leafs 0
For most teams, that's one good power play. For others, it's one lacklustre period. For the 1999–2000 Maple Leafs, facing the Devils with their season on the line, it was an entire game.
The performance set a modern NHL record for the fewest shots in a game (regular season or playoffs), and made for a humiliating way to end a season.
So did the Maple Leafs really have just six shots that night? Probably not – the Devils were known for undercounting opponent totals, and even in the aftermath of the loss, Leafs players insisted they'd managed at least twice as many. Still, it was a humbling performance no matter how you counted it.
No. 6: 1988 Norris Division semi-finals, game four: Red Wings 8, Maple Leafs 0
In the best playoff games post, we reminisced a bit about the miserable Harold Ballard era that finally ended with the 1993 run. It was in full swing by 1988, when the Maple Leafs snuck into the Norris playoffs despite a pathetic 52-point showing. Game four was the night that the team hit rock bottom, and that fan frustration finally boiled over.
With the Leafs on the receiving end of a 8–0 thumping, fans wearing bags over their heads pelted the ice with garbage, pucks and souvenir "Brophy's Boys" hats. They booed mercilessly. And then came the jerseys.
Modern-day fans seem to think that a few waffles counts as some sort of insurrection. Back in 1988, a beaten-down Leafs team would have probably viewed a few frozen breakfast treats as a peace offering.
No. 5: 2001 Eastern Conference semi-finals, game seven: Devils 5, Maple Leafs 1
The 2000–01 Maple Leafs were the worst regular-season team of the Quinn era, finishing with just 90 points. But they looked like a different team in the playoffs, sweeping the Senators aside in the opening round and then earning a seventh game against the same Devils team that had served up that six-shot debacle a year before.
But instead of revenge, the Leafs absorbed a loss that was somehow even worse. They took a 1–0 lead into the first intermission, but that was where the good news ended. The Devils exploded for three goals in the second and cruised to an easy 5–1 win.
The series is probably best remembered for Tie Domi's vicious elbow on Scott Niedermayer in the dying moments of game four. It's come to be remembered as the turning point of a series the Leafs were firmly in control of until Domi's cheap shot woke up the Devils and inspired them to victory. That doesn't quite match up with reality — the Leafs actually went out and won the next game in New Jersey — but it's the narrative that's largely stuck.
But even putting the Domi hit aside, the game seven loss to the defending Cup champs was a tough one to swallow for Toronto fans; despite the early success of the Quinn era, the Devils served up a reminder of just how far the Leafs still had to go.
No. 4: 1994 Western Conference final, game five: Canucks 4, Maple Leafs 3 (2OT)
The 1993–94 playoffs seemed to present the Leafs with a straightforward path to the Cup final. After knocking off the Blackhawks in round one, Toronto was left as the conference's top remaining seed, and after disposing of the surprisingly feisty Sharks, they met the seventh-seeded Canucks in round three. That matchup seemed winnable, especially after Peter Zezel's overtime goal took game one.
But the Canucks won game two, and the series shifted to Vancouver for three straight under the league's short-lived 2-3-2 format. The Leafs' goal was clear – make it back to Toronto for games six and seven. A pair of shutout losses put them behind 3–1 in the series, but they came out flying in game five, jumping out to a three-goal lead and seemingly booking their trip back home.
Instead, they coughed up the lead. The Canucks sent the game to overtime, where Greg Adams ended it early in the second extra frame.
That's an all-time Sad Goalie Slump by Felix Potvin right there. The Leafs wouldn't win another round for five years.
No. 3: 2013 Eastern Conference quarter-finals, game seven: Bruins 5, Maple Leafs 4 (OT)
Admit it — you thought this was going to be No. 1.
There's a great case to be made. Taken on its own, it may be the most devastating game any team has endured in recent memory. It's so bad that you know all the details, even if you're not a Leafs fan — the 4-1 lead, the late collapse, and then the inevitable overtime dagger.
It's still painful to this day, so much so that a video of Maple Leaf fans merely watching it is almost unbearable. If you're a fan of another team and you want to twist the knife on a Leafs' supporter, this is probably your go-to game.
So how is it not No. 1?
Well, for one thing, the 2013 Maple Leafs weren't all that good. They were underdogs against the Bruins, and nobody expected them to go deep into the playoffs. As painful as the ending was, nobody thinks it cost them a shot at the Cup.
But more importantly, this is where hindsight shows up. If you're a Leafs fan, imagine an alternate universe where Matt Fratin buries his breakaway and the Maple Leafs win the series. Where are they today?
Remember, the 2013 Leafs had an expensive core that largely underachieved, a coach who introduced "mind-boggling" into the local sports lexicon, and a front office that thought David Clarkson was a good idea. Despite all that, they snuck into the playoffs in a lockout-shortened season, which was somehow good enough for the CEO to start planning parade routes and handing out extensions.
If they actually beat the Bruins, does Brendan Shanahan show up a year later? Do Mike Babcock and Lou Lamoriello follow? Do they draft finesse players like William Nylander and Mitch Marner? Do they hit rock bottom and draft Auston Matthews? Are they anywhere near where they are today?
Probably not. In a weird way, that collapse against the Bruins was one of the best things that ever happened to the franchise.
Hindsight only takes you so far; the Boston debacle was still an absolute kick in the gut for Leafs fans at the time, and remains so to this day. It was bad then, and even with the benefit of some rose-coloured glasses, it's bad today.
It's just not quite the worst.
No. 2: 2004 Eastern Conference semi-finals, game six: Flyers 3, Maple Leafs 2 (OT)
Much like the 2013 collapse looks slightly better in hindsight, the 2004 loss to the Flyers just gets worse as time goes on. It followed an opening-round win over the Senators that remains, to this day, the last playoff round won by the franchise.
While nobody knew just how bad the decade to come would be, there was already a sense of urgency around the 2003–04 Leafs. The Quinn era had produced seven series wins and two trips to the conference final, but the team was getting older, and with a potentially season-scrapping lockout looming, the team's window felt like it could be closing.
But if they had a shot at finally ending the Cup drought, this roster seemed like the one to do it. They'd just put up a team-record 103-point season, and new GM John Ferguson had gambled a chunk of the future to bring in Brian Leetch at the deadline. This was probably the single best Maple Leafs team of the post-1967 era, period.
But it didn't matter. After knocking off the Senators, the Leafs dropped the first two against the Flyers. They'd tie the series up with two home wins, only to get their doors blown off back in Philadelphia in a humiliating 7–2 loss. Facing elimination at home, they sent the game to overtime, where an old friend from the Norris Division days delivered the fatal blow.
The goal itself was crushing, but the sequence that led up to it made it even worse. The shift included Darcy Tucker's memorable obliteration of Sami Kapanen, followed by a Flyers two-on-one that saw Mark Recchi turned aside by Ed Belfour.
Those two plays had the crowd on its feet. It was almost as if the hockey gods waited just long enough for every Maple Leafs fan to think "maybe they're really going to pull it off" before crushing their hopes once and for all.
No. 1: 1993 Campbell Conference final, game seven: Kings 5, Maple Leafs 4
In the 24 years since the 1992–1993 season, the Maple Leafs have had some deep runs. If we're being honest, they've had better teams. But what they haven't had is the feeling that had surrounded the team heading into the series against the Kings: That this was the year. Other Leafs teams have been good enough to win. This was the one that felt destined to.
Everything that had led up to game seven – the rebuild, the comebacks, the overtime winners, the solo efforts, the way the team just kept finding a way – had made it clear. This was the year. And with the Montreal Canadiens waiting in the final, there was no way that the Kings were going to walk into Maple Leaf Gardens and ruin it all in game seven.
That's why this game tops our list, instead of the one from this series you might be expecting to see, the Kerry Fraser game. The Kings' overtime win in game six may well be the most controversial game in Maple Leafs history, and lord knows no Toronto fan has stopped complaining about it ever since. But painful? Not really. That game featured Wendel Clark's hat trick and a suitable villain in Fraser, and at the time we all just figured it was setting the stage for what came next. Of course the series had to end in seven, just like Detroit and St. Louis before it. We had this.
So when the Leafs fell behind 2–0 after one, no problem. We knew they'd come back, and they did. When they were behind 3–2 heading into the third, no problem. We knew they'd come back, and they did. When the Kings took a 5–3 lead late in the third, even on a goal as ridiculous as Wayne Gretzky's bank shot off Dave Ellett's skate, we knew they'd come back.
And sure enough, they did... almost. The Leafs closed the gap to 5–4 and then poured on the pressure late. There may not be a more cynical, pessimistic fanbase in pro sports than the Toronto Maple Leafs', but for one moment, maybe the only moment, we all believed.
And then the puck trickled over the line, the final horn sounded, and it was over.
Wayne Gretzky later called it the greatest game he ever played, and maybe hearing that from the best player who ever lived should dull the pain. It doesn't. Nearly a quarter of a century later, this remains as close as the Maple Leafs have ever been to the Cup.