Here we go again.
This has to be the year the º£½ÇÉçÇø¹ÙÍøMaple Leafs — who haven’t won a series in 19 years but now holds the longest active NHL playoff streak with the Bruins (seven seasons) — get past the first round, right? Right?
It has to be. The evidence is there: Second-best franchise record in points with 111, valuable additions at the trade deadline of Ryan O’Reilly, Jake McCabe, Noel Acciari and more, plus a solid season from Ilya Samsonov in net. While it’s another matchup with the Tampa Bay Lightning, who won back-to-back Stanley Cups in 2020 and 2021 and disposed of the Leafs in seven games last year, the odds might still be in Toronto’s favour.
As of Tuesday morning according to , the Leafs had 59.8 per cent chance of making the second round compared to the Lightning’s 40.2 per cent. Either way, it’s going to be tight, and if you’re thinking like the Star’s Kevin McGran, then the series might really come down to who’s better in goal.
History offers valuable lessons, so what better way for Leafs fans to mentally prepare for this year’s playoffs than by reminding themselves of the pain in the first round to get to this point. So let’s get the déjà vu and glitch-in-the-Matrix jokes out of the way and take a trip down memory — or nightmare — lane.
And just think about how good it’ll feel when the proverbial playoff curse breaks (or it doesn’t. In that case, see you next April).
Editor’s note: most of this timeline was written ahead of last year’s playoffs, but has been updated with the 2022 results.

º£½ÇÉçÇø¹ÙÍøMaple Leafs goalie James Reimer lays on the ice after getting beat on the game winning goal by Boston Bruins center Patrice Bergeron during overtime in Game 7 of their NHL hockey Stanley Cup playoff series in Boston, Monday, May 13, 2013. The Bruins won 5-4.
Charles Krupa/The Associated Press2013 | ‘But they were up 4-1 . . .’ Lost to Bruins, 4-3
Possibly the most infamous of them all. Game 7 of this series is so well known that there are videos of so you can relive it by laughing or crying (or both maybe).
Ask any Leafs fan and they can tell you the exact moment where they were when Patrice Bergeron stuck a dagger into their heart about six minutes into overtime.
The Leafs, playing in their first playoff series since 2004, weren’t the favourites to win, and after going down 3-1 through the first four games, hopes weren’t high that they could come back.
But after impressive Game 5 and 6 wins — mostly due to strong performances from James Reimer between the pipes — the Leafs forced a Game 7. Momentum was on their side, and the Leafs held a stunning 4-1 lead in the third. However, it only took half a period and a raucous Bruins crowd for everything to come crashing back down to Earth.
The rest is history. It was the first time in NHL history that a team trailing by three goals in the third period of a Game 7 came back to win.
The image of Reimer, sprawled face down in the crease, symbolized how every Leafs player and fan felt in that moment.
2014-16 | Return to the Dark Ages. No playoff appearances
We don’t need to talk about this. (But remember the Peter Horachek era?)

º£½ÇÉçÇø¹ÙÍøMaple Leafs centre Mitch Marner (16), centre Tyler Bozak (42) and defenceman Martin Marincin (52) look on as the Washington Capitals celebrate their win during the first overtime period of game six in an NHL Stanley Cup hockey first-round playoff series in º£½ÇÉçÇø¹ÙÍøon April 23, 2017.
Nathan Denette/The Canadian Press file photo2017 | Emergence of Matthews, Marner — and hope. Lost to Washington Capitals, 4-2
It was the first full season with Auston Matthews, Mitch Marner and William Nylander, and second under head coach Mike Babcock. The tide had finally turned and the Leafs were beginning to lay the foundation for what they would become.
Expectations at the beginning of the season were still low, and no one would’ve been surprised if they had missed the post-season again, but after a late push, the Leafs squeaked in and faced off against the Presidents’ Trophy winners, the Washington Capitals.
It was a lot of closer than most were expecting. Each game was decided by a single goal, and five of the six had gone to overtime, only the third time that’s happened in NHL history.

º£½ÇÉçÇø¹ÙÍøMaple Leafs goaltender Frederik Andersen looks back as the puck bounces to the back of the net on a goal by Boston Bruins right wing David Pastrnak (88) during the third period of Game 7 of an NHL hockey first-round playoff series on April 25, 2018.
Charles Krupa/The Associated Press file photo2018 | A 2013 redux? Lost to Bruins, 4-3
It almost felt like it was 2013 all over again. It was a classic back-and-forth affair, with high scoring and bad blood. The mood started sour for the Leafs, however, after key centre Nazem Kadri was suspended three games for charging in Game 1 and then º£½ÇÉçÇø¹ÙÍøfound themselves in an early 2-0 series hole. The Leafs came back again and lost — again — despite a brief lead in Game 7 in Beantown.

Nazem Kadri of the º£½ÇÉçÇø¹ÙÍøMaple Leafs reacts after a fight with Jake DeBrusk of the Boston Bruins in Game Two of the Eastern Conference First Round during the 2019 NHL Stanley Cup Playoffs at TD Garden on April 13, 2019 in Boston, Mass.
Adam Glanzman/Getty2019 | A 2018 redux? Lost to Bruins, 4-3
It almost felt like it was 2018 all over again. It was a classic back-and-forth affair, with high scoring and bad blood. The mood started sour for the Leafs, however, after key centre Nazem Kadri was suspended . . . wait a minute. Déjà vu?
Yes, you read — or remember — that correctly. Game 1 may have been a win for the Leafs, but Kadri was suspended in Game 2 for the rest of the series for cross-checking Jake DeBrusk in the head. It would also be the last time Kadri would wear the blue and white.
The series again went to Game 7 in Boston, but it wasn’t as tight as previous ones. The Leafs lost 5-1, and scampered into the off-season at the hands of the big, bad Bruins.

Auston Matthews reacts after his team was defeated 3-0 by the Columbus Blue Jackets after Game Five of the Eastern Conference Qualification Round at Scotiabank Arena on August 09, 2020 in Toronto.
Chase Agnello-Dean/Getty2020 | Technically didn’t even make it. Lost in qualifying round to Blue Jackets, 3-2
After a three-month hiatus due to the COVID-19 pandemic, the NHL resumed in late July with bubbles in º£½ÇÉçÇø¹ÙÍøand Edmonton for the playoffs. Since the season was cut short, a number of teams had to play in best-of-five qualifying rounds to determine seeding.
The Leafs were spared another meeting against the Bruins and were the heavy favourites against the Blue Jackets. But playoff woes persisted, and the Leafs were fooled by goalie Joonas Korpisalo, who had two shutouts, including one in the deciding Game 5. The only bright spot was that fans couldn’t witness this collapse in person.

Montreal Canadiens shake hands with the º£½ÇÉçÇø¹ÙÍøMaple Leafs after the conclusion of their 2021 first round series.
Steve Russell/The º£½ÇÉçÇø¹ÙÍøStar file photo2021 | Historic matchup with history repeating. Lost to Canadiens, 4-3
A new division featuring all Canadian teams was constructed specifically for the 2020-21 season, adding a new dynamic to matchups and rivalries. The Leafs won the division in the regular season, the first time they had finished atop one since 2000.
There was no possibility the Leafs would even face the dreaded Bruins in the first round, so they were matched against the Montreal Canadiens for the first time since 1979.
Instead of climbing back and collapsing, the Leafs were on the verge of winning ... and then collapsed. º£½ÇÉçÇø¹ÙÍøwas up 3-1 and were in the driver’s seat for most of the series despite a gruesome injury to captain John Tavares in Game 1. But Carey Price was unstoppable, and the Leafs lost the final three games.

º£½ÇÉçÇø¹ÙÍøMaple Leafs and Tampa Bay Lightning players shake hands after the Round 1 NHL Stanley Cup Playoffs Game 7 between the Tampa Bay Lightning and the º£½ÇÉçÇø¹ÙÍøMaple Leafs on May 14, 2022, at Scotiabank Arena in Toronto.
Icon Sportswire2022 | Taking on the champions. Lost to the Lightning, 4-3
It was a historic season.
The Leafs were a powerhouse all year, sitting second in the Atlantic Division with a franchise record 115 points. Matthews scored 60 goals, another franchise first. There was home ice advantage for Toronto, and despite the series being against the defending Stanley Cup champions, momentum was on the Leafs’ side.
It started off well for the Leafs. Led by two goals from Matthews and a strong performance from goalie Jack Campbell, º£½ÇÉçÇø¹ÙÍøcame roaring out of the gate with a 5-0 win over Tampa in Game 1. The Lightning would bounce back to send the series back tied to Tampa.
The two sides traded victories over the next three games so the Leafs had a chance to close out the series in Game 6. The Leafs clawed back from two-goal deficit to force overtime, but eventually lost, sending the two teams back to º£½ÇÉçÇø¹ÙÍøfor the deciding seventh game — a trend Leafs fans were quite used to at this point.
History indeed repeated itself. Tampa, led by a two-goal performance by Nick Paul, held off º£½ÇÉçÇø¹ÙÍøand took the series with a 2-1 win. It was the Leafs’ eighth consecutive playoff series loss and 10th consecutive loss in series-clinching games.
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