The Leafs’ best win and worst loss against each Canadian team

We’re a week into the season. How are you feeling about the all-Canadian schedule so far, Leafs fans?

I’m guessing you’re enjoying it, because right now it still feels new. Sure, there may come a point where seeing the same teams over and over starts to lose some lustre, and Leafs fans find themselves missing the occasional meeting with rivals like the Red Wings, Sabres or even the Bruins. But for now, it’s been pretty great.

So today, let’s remember some of the best and worst of the Leafs’ history in all-Canadian matchups. We’ll go through each of the six opponents in this year’s North Division, and come up with both the Leafs’ best win and worst loss against those teams.

These picks are subjective, obviously, and I’m sure a few of you will have your own picks for some of them. That’s half the fun, since we can use the comment section to Remember Some Games. But here are my picks for the best and worst of the Leafs against Canadian opponents.

Leafs vs. Senators

We’ll start with what’s probably the easiest team to find games for. The Leafs and Senators have both the least history (because it only dates back to 1992) and the most (because of all those Quinn-era playoff matchups), and plenty of it has been memorable.

Best win: Leafs 4, Senators 1 – April 20, 2004

There’s no shortage of candidates for the best game when you’re talking about an opponent you’re 4-0 against in the postseason, but I think this one is the clear winner. It wasn’t the closest game or even the most entertaining, but it’s the one that’s come to symbolize the pre-cap Battle of Ontario. Joe Nieuwendyk’s pair of softies turned what figured to be a tense Game 7 showdown into a relatively easy Leafs win, spelling the end of the Jacques Martin era in Ottawa. It remains the Leafs’ last playoff series win, against Ottawa or anyone else.

Worst loss: Senators 8, Leafs 0 – October 29, 2005

One of the weird postscripts to the four-part playoff arc was that while the two teams have never met in the postseason after the lockout, there was a period when the Senators would consistently embarrass the Leafs in regular season meetings. I went with this 8-0 rout in Toronto, but we could also go with a 7-0 loss in Ottawa a few months later, or a pair of 8-2 options. Did it erase the pain of losing four straight in the playoffs for Sens fans? Not really, but every little bit helps.

Other candidates: Any number of memorable playoff moments, including wins like the triple-OT Gary Roberts game, the 2002 Game 7, the comeback in Game 6 of that same series, or sudden death winners from Mats Sundin, Cory Cross, Stumpy Thomas. On the loss side of the ledger, there was a 5-0 blowout in the 2002 opener, and the NHL’s first-ever shootout defeat. There was that awful Bryan Berard game. And the rivalry has also given us memorable moments like the flu game, the fake stick throw, Chara vs. McCabe, and Tucker vs. the bench, plus a more recent memory in Auston Matthews’ record-breaking four-goal debut, which I’m going to just go ahead and say the Leafs must have won.

Leafs vs. Oilers

They’ve never met in the playoffs, but did almost pull off the biggest trade in sports history. They also may be the two most neurotic fan bases in the league, so hockey gods help us if they actually do get a postseason matchup this year.

Best win: Leafs 11, Oilers 9 – January 8, 1986

For pretty much all of the 1980s, the Oilers were good and the Leafs were awful and the games between them went pretty much exactly the way you’d expect them to. The decade saw the Oilers beat the Leafs by scores of 9-1, 8-3 (twice), 8-2, 9-2, 8-5, 9-5, 7-1 (twice) and 9-4. And in most of those games, you felt like Edmonton was going easy on them.

So it was a remarkable night in 1986 when the Leafs not only got a rare win against the Gretzky-era Oilers, but did it by beating them at their own game. In what still stands as the highest-scoring Leafs game ever (and just one goal away from the record for highest-scoring game in NHL history), the Leafs jumped out to a 3-0 lead and then went up and down the ice with a dynasty. Gretzky finished with six points, but the Leafs got three from Russ Courtnall, Steve Thomas and rookie Wendel Clark, and a four-goal night from Miro Frycer.

A personal note on this game: The kids in my school were losing their minds the next day. It was right up there with the discovery of the Super Mario warp trick, and met with just as much skepticism. Even at that young age, we knew not to believe in good things happening to the Leafs.

Worst loss: Oilers 7, Leafs 5 – December 18, 1991

We could pick any of those 1980s blowouts, but I’m going with an only slightly more recent option. In 1991, Cliff Fletcher had just arrived, and his first major blockbuster was a seven-player blockbuster with the Oilers that brought Grant Fuhr and Glenn Anderson to Toronto. This was the first game between the two teams after that deal, and a chance for the rebuilt Leafs to serve notice that they were for real. But then Fuhr got shelled, Vince Damphousse had two points in his return to Toronto, and Peter Ing didn’t just beat his former team, he earned one more point than Anderson while doing it.

Other candidates: The recent game where Kris Russell scored the winner into his own net and Nazem Kadri laughed at him. Wendel Clark’s four straight goals in 1996. It doesn’t count because it wasn’t a game, but we have to mention the Leafs “losing” the McDavid lottery to the Oilers on the final ball. And while the infamous waffle game didn’t come against the Oilers, they get partial credit because the guy who threw them was apparently wearing an old school Gretzky jersey.

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50 years without a Cup: Are the Leafs really the NHL's most miserable team?

Today is an important anniversary for Toronto Maple Leafs fans.

You’ll notice I didn’t say “happy anniversary,” since this isn’t exactly a day that Leafs fans will want to celebrate. Oh, it marks the anniversary of a happy moment in franchise history; it was 50 years ago tonight that George Armstrong’s iconic empty-net goal sealed a 3–1 win over the Canadiens, securing the franchise’s 13th Stanley Cup.

The not-so-happy part is what’s happened in the 50 years since. Or, more accurately, what hasn’t happened. A full five decades later, the Maple Leafs are still stuck on 13 Cups, as the team’s championship drought has officially reached the half-century mark.

We’ve known this milestone was coming for a while now; it’s been clear for just about the entire salary-cap era that the Maple Leafs weren’t going to win a Cup any time soon. But there’s hope in Toronto these days, as the best collection of young talent the team has had in a generation seems to be on its way towards contending again, maybe as early as the next year or two. For the first time in ages, there’s some genuine optimism that the drought could end someday soon.

Still... 50 years. Man, that's a long time. I wasn't alive back then. You probably weren't either. We knew this day was coming, but it still feels like a big number. From Harold Ballard to Kerry Fraser to JFJ to 4–1, it's been a rough stretch for long-suffering Leafs fans.

But all that said, have the Maple Leafs really been the NHL's most miserable team over the last half-century? After all, it's not like they're the only team that hasn't won a Cup since 1967. That list is actually a reasonably long one, meaning even if we rule out one-off teams like the Rangers and Flames, we're still left with a dozen Cup-less candidates.

So today, as we celebrate Toronto's dubious anniversary, let's compare them to the other teams that haven't won a championship since 1967, and try to figure out how they stack up against the Maple Leafs track record of misery.

St. Louis Blues

The history: Of all the teams who haven’t won a Cup in the post-1967 era, the Blues join the Leafs as the only one that actually existed back in 1967. And only barely; they took the ice for the first time as an expansion team that fall. That's led to an ongoing argument over whether the Blues and Leafs are tied for the NHL's longest Cup drought or whether the Leafs technically own the claim outright, which has to be just about the saddest sports debate there can be.

Closest call: The Blues went to the Stanley Cup Final in each of their first three seasons, which sounds impressive until you remember that the NHL stuck all its terrible expansion teams in the same division, guaranteeing one of them a spot in the final. The Blues were the best of the worst all three years, but got swept each time and haven't been back since.

Low point: The 1999–2000 Blues won 51 games and the Presidents' Trophy, heading into the playoffs as Cup favourites. Seven games later, they were out in the first round, thanks largely to this long-distance goal:

They might be even worse than the Leafs at: Drafting. Like Toronto, the Blues have been better lately (the Vladimir Tarasenko pick was genius). But this is still the team that took Erik Johnson over Jonathan Toews in 2006, which not only set them back but also helped a division rival build a dynasty. And as bad as the Leafs have been, at least they never no-showed a draft entirely.

But at least: From 1980 through 2004, the Blues made the playoffs in 25 straight seasons. These days, the Leafs are hoping to just get there in back-to-back years.

Are they worse?: This one is closer than you think, especially since the Blues' three trips to the final don't really count. But their general consistency and lack of truly rock-bottom moments leaves them a notch behind Toronto on the misery scale.

Washington Capitals

The history: While they give the Leafs a decent head start by not existing until 1974, the Capitals gain that ground back quickly by immediately posting the worst season in modern NHL history. The 1974–75 Caps team managed just 21 points, and the team didn't make the playoffs until 1983. And then things got bad.

Closest call: The Caps at least made it to the 1998 Cup final, although they didn't win any games once they were there.

Low point: At the rate things are going, check back in a few days.

They might be even worse than the Leafs at: Protecting series leads. The Capitals have a stunning history of repeatedly blowing two-game leads in the playoffs; it's kind of their thing. Granted, it's not like Leaf fans can get all high and mighty about protecting playoff leads, but the Caps have dedicated decades to their craft.

But at least: The Capitals have won three Presidents' Trophies in the last eight years; the Maple Leafs have only topped 100 points once in their history.

Are they worse?: This one may be too close to call. The Caps have had lower lows, both in the regular season and playoffs. But they've also had higher highs, including that one trip to the final. Let's see just how heart-breakingly this season ends before we make any final decisions.

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