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Stanley Cup Droughts: 5 Groups Who’ve Been Ready the Longest For One other Title

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May 29, 2025
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Stanley Cup Droughts: 5 Groups Who’ve Been Ready the Longest For One other Title
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In just some brief weeks, a brand new champion within the NHL might be topped, and one of many closing 4 contenders has waited a long time for the possibility to win again Lord Stanley’s Cup.

The final time the Edmonton Oilers received the Stanley Cup was in 1990, once they defeated the Boston Bruins in 5 video games, regardless of the absence of Wayne Gretzky, who had been traded to Los Angeles in the summertime of 1988. 

Whereas Connor McDavid might lead the Oilers again to a Stanley Cup win this June, 4 different groups who’ve been ready even longer won’t have an opportunity to win the Cup. 

What follows are the 4 longest Stanley Cup droughts nonetheless going within the NHL. 

Please observe that groups which have by no means received the Cup will not be included on this checklist, which makes good sense to me. You’d by no means say it’s been 20 years because you’ve eaten a scorching canine in case you’d by no means eaten a scorching canine earlier than. 

1. Toronto Maple Leafs

I believed the Maple Leafs had an opportunity to finish their drought this season, however it’ll be one other yr in ready for the followers who haven’t seen a Cup in 57 years. 

The final time the Stanley Cup was received in Toronto was in 1967. For reference, in that yr, the NHL nonetheless had solely six groups, we have been nonetheless two years away from the Moon touchdown, McDonald’s launched the Large Mac, and Wayne Gretzky was six years outdated. 

The ‘67 title was the thirteenth for the Maple Leafs and featured the oldest lineup of gamers ever to win the Cup, with a mean age of 31. 

Toronto defeated the Chicago Blackhawks in six video games after which went on to beat the Canadiens within the Finals, additionally in six video games. 

Since then, the Maple Leafs have by no means returned to the Stanley Cup Finals regardless of 5 appearances within the Convention Finals. The closest they received was in 1993 once they confronted the Gretzky-led Kings. They misplaced 5-4 at dwelling in Recreation 7 by the hands of a Gretzky hat trick. 

Toronto had a stable probability to win the Cup lately with its star-studded ‘Core 4’ of Auston Matthews, Mitch Marner, John Tavares, and William Nylander. However with Marner prone to go away this offseason, the window of competition for that group could also be shut. 

2. Philadelphia Flyers

Philadelphia’s final Stanley Cup got here 49 seasons in the past in 1975 in the course of the famed Broad Avenue Bullies period of the group. 

1975 was the second of the back-to-back titles for the Flyers, the one two championships in franchise historical past. Philadelphia superior to the Finals after sweeping the Maple Leafs within the first spherical after which beating the Islanders in seven video games. 

The ‘75 Finals, the place the Flyers met the Buffalo Sabres, was the primary performed between two non-Unique Six groups. Philadelphia received the sequence in six video games. 

The sequence can be well-known for Recreation 3 in Buffalo, the place the sport was delayed twice as a consequence of fog within the area and a bat flying above the gang. Sabres middle Jim Lorentz killed the bat together with his stick, incomes him the nickname Batman from teammates, and area staff skated across the ice waving mattress sheets to minimize the fog. 

Since then, the Flyers have returned to the Finals six extra instances, most not too long ago in 2010. 

Now the group is in a protracted state of rebuilding, having missed the playoffs in 5 straight years and 7 of their final 10 seasons. 

Philadelphia not too long ago made a training change, although, swapping out John Tortorella for Flyers Corridor of Famer and former Vancouver Canucks head coach Rick Tocchet. 

3. New York Islanders

New York has the third-longest Stanley Cup drought within the NHL, spanning 41 years, with its final title coming in 1983.

The Islanders ripped off 4 straight within the late Seventies and early Eighties, the one championships of their group’s historical past. 

New York arrived on the Finals after defeating the Capitals in 5 video games, the Rangers in six, and the Bruins in six within the earlier rounds. Within the Finals, they met the Edmonton Oilers, their first look within the championship sequence as a franchise. 

The Islanders received the sequence in a dominant sweep with a formidable efficiency from the Conn Smythe-winner, goaltender Billy Smith. Smith had a 2.68 GAA and a .912 save share in these playoffs, the spotlight of which got here when he shut out the legendary Gretzky-led Oilers scoring group. 

No group in North American skilled sports activities has received 4 consecutive titles since this New York group did it. 

However because the dynasty within the Seventies and Eighties, there hasn’t been a lot else to have a good time for Islanders followers. They misplaced within the Stanley Cup Finals the next yr in a rematch towards Edmonton. Following the 1987 season, the group went twenty years with out successful a playoff sequence. 

They underwent an unpleasant rebrand within the Nineteen Nineties, which followers hated. They have been virtually bought by a Dallas businessman named John Spano, who turned out to be pretending to be a lot wealthier than he was and subsequently hung out in jail on fraud costs associated to his tried buy. 

The group additionally briefly relocated to Brooklyn’s Barclays Heart within the 2010s, an area particularly designed for basketball, earlier than constructing a brand new area on Lengthy Island. 

New York has the primary decide within the upcoming draft, however they’re nonetheless a great distance away from being near competition once more. 

4. Calgary Flames

Final on our checklist, with the 4 longest Stanley Cup drought, is the Calgary Flames, who haven’t received since 1989. 

It’s inarguably the apex of the Flames franchise, provided that it’s their first and solely championship in group historical past. That very same yr, they have been additionally division champions (their second of three division titles) and Presidents’ Trophy champions (their second and most up-to-date win). 

Maybe this title requires an asterisk as a result of Calgary was capable of advance to the Cup Finals primarily as a result of their greatest rival and convention menace that season, the Oilers, have been eradicated within the first spherical by the Los Angeles Kings. 

They received their opening spherical sequence towards Canucks in seven video games, then beat the Kings in a sweep, and superior to the Finals after Chicago within the Convention Finals in six video games. 

They then met the Montreal Canadiens, in the newest assembly of two Canadian groups within the Stanley Cup Finals, and received the sequence in six video games. 

After that title, the Flames didn’t win a playoff sequence once more till the 2003 season, once they returned to the Stanley Cup Finals and misplaced to the Tampa Bay Lightning. Since then, they’ve solely made it previous the primary spherical of the playoffs twice. 

This additionally permits me to debate the extremely unusual and stacked Calgary groups of the late 2010s and early 2020s, who inexplicably did not make any important noise within the playoffs. 

The groups featured the late nice Johnny Gaudreau because the star alongside one of many present faces of the NHL, Matthew Tkachuk. The groups have been invariably rounded out by some mixture of Sam Bennett, Elias Lindholm, Noah Hanifin, Nikita Zadorov, and Chris Tanev. 

When you’re a Flames fan you’re painfully conscious of this, and I’m sorry for rubbing salt within the wound, however it’s simply one of many strangest conditions in current NHL reminiscence. 



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