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When was the last time the Toronto Maple Leafs won a playoff series?

The forlorn franchise hasn’t gotten to the last eight of the Stanley Cup Playoffs in quite awhile.

Auston Matthews of the Toronto Maple Leafs looks to pass in the second period during Game Six of the First Round of the 2023 Stanley Cup Playoffs against the Tampa Bay Lightning at Amalie Arena on April 29, 2023 in Tampa, Florida. Photo by Mike Ehrmann/Getty Images

The Toronto Maple Leafs have advanced to the second round of the Stanley Cup Playoffs with a 4-2 series win over the Tampa Bay Lightning following a 2-1 overtime win in Game 6 of their first round series on Saturday night in Tampa.

The Leafs needed three overtime road wins at Amalie Arena to advance, but for the core of Auston Matthews, Mitch Marner, and John Tavares, they have finally gotten the monkey off their back. And for an Original Six city that has been without a title since 1967, it’s at least one step closer to a parade that would set Ontario ablaze.

Toronto had lost 11-straight games that would have put them in the next round of the Playoffs, but they have finally made it to Round 2 for the first time since 2004. That team led by Mats Sundin and Ed Belfour knocked off the Ottawa Senators in seven games before falling to the Philadelphia Flyers in six.

But this year’s edition will now face the winner of Game 7 between the Florida Panthers and Boston Bruins. The Bruins are the President’s Cup winners and were one of the best two-way teams in NHL history during the regular season, and they’d be a significant favorite if they can get past an upstart Florida.

If the Leafs do reach the Eastern Conference Final, they’ll be the first TO team to get to the NHL’s last four since 1999.