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NHL: 30 best series winning goals in NHL Playoffs history

By Nick Villano

St. Louis Blues left wing Pat Maroon (7) is congratulated by teammates after scoring the game winning goal in double overtime in game seven of the second round of the 2019 Stanley Cup Playoffs against the Dallas Stars at Enterprise Center. Mandatory Credit: Jeff Curry-USA TODAY Sports
St. Louis Blues left wing Pat Maroon (7) is congratulated by teammates after scoring the game winning goal in double overtime in game seven of the second round of the 2019 Stanley Cup Playoffs against the Dallas Stars at Enterprise Center. Mandatory Credit: Jeff Curry-USA TODAY Sports /
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Philadelphia Flyers
Center Jeremy Roenick #97 of the Philadelphia Flyers (Photo by Jeff Gross/Getty Images) /

NHL: 30 best series-winning goals in NHL playoff history:
27. Jeremy Roenick beats the Maple Leafs

Hockey fans have been hearing about 2004 a lot lately. That’s because it was the last time the Toronto Maple Leafs won a playoff series. After blowing a 3-1 series lead to the Montreal Canadiens in 2021, it seems like that might be the last time it happens. Either way, it was a back breaker of a loss.

The Leafs took on the Philadelphia Flyers in the second round. They were one of the best teams in the Eastern Conference, so the Leafs had a long hill to climb. The Leafs went down in the series 2-0, but they won both games back in Toronto to even things up. After losing again in Philly, they went back to the Air Canada Centre where the Leafs were undefeated in the series.

The Flyers took a 2-0 lead in the first period. It seemed like they had the Leafs’ number when they held that lead into the third period. Then, Karel Pilar finally broke the wall that was Robert Esche. There were less than 11 minutes left in the game, but the Leafs were in it. Six minutes later, and the Leafs’ star was on the case. Mats Sundin tied the game with less than five minutes left. Elation at the Air Canada Centre.

In overtime, it was all for naught.

The play was absolute craziness. The Leafs were driving on Esche, but then the Flyers got a two-on-one that John LeClair ended up taking a shot on. The play went the other way, and Sundin got another chance that was blocked. The play went the other way again, and Jeremy Roenick shot the puck rather than pass it. He beat Ed Belfour, and the Flyers were in the Eastern Conference Finals. This would be the last time the Leafs would see the second round of the playoffs, and it ended like this.

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