Which NHL Teams Have the Longest Stanley Cup Droughts?

The Carolina Hurricanes had a two-decade break in between their two Stanley Cup wins as a franchise, but that “drought” is nothing compared to some of the other NHL franchises. 

I’m sure that fans of the five teams in the league with the longest Stanley Cup droughts would do anything for a measly 20 years in between titles. Some of the league’s most historic teams, with some of the most dedicated fanbases in the league, have been waiting nearly three times that to see their team hoist the Cup.

Here’s a look at the five teams with the longest Stanley Cup droughts and a look at whether any of them can end it in 2027.

Which NHL Teams Have the Longest Stanley Cup Droughts?

5. New York Islanders, 42 seasons

Long Island fans have been waiting four decades to see their team back at the NHL mountaintop. 

The Islanders had a dynastic run in the early 80s, winning the Stanley Cup four years in a row in 1980, ‘81, ‘82, and ‘83. No team has been able to string together four Cups in a row. 

That run had five Hall of Famers: captain and defenseman Denis Potvin, goalie Billy Smith, as well as forwards Bryan Trottier, Mike Bossy, and Clark Gillies. 

The Islanders went back to the Stanley Cup Finals in 1984, losing in five games to the Oilers, and have not returned since. 

In the following decades, the team had to deal with being moved off Long Island and then back again. They’ve dealt with crooked ownership groups. And above all, they’ve struggled to recapture the glory of those 80s teams.

Things are looking up for New York, though, after landing the first overall pick in last year’s entry draft and drafting defenseman Matthew Schaefer, who projects to be a generational talent. Schaefer won the Calder Trophy last season and helped the Islanders improve on their points total.

Ahead of the 2026-27 season, New York is a +8000 longshot to win the Stanley Cup and has +3500 odds to win the Eastern Conference.

While the Islanders probably aren’t ending the drought in the next couple of seasons, they’re moving in the right direction now. 

4. Philadelphia Flyers, 50 seasons

Philly fans haven’t seen their team hoist the Stanley Cup since the era of the ‘Broad Street Bullies’ in the 1970s. 

The Flyers won the Cup in back-to-back seasons in 1974 and 1975, led by captain Bobby Clarke, who was inducted into the Hall of Fame in 1984. 

The team earned the moniker of ‘Broad Street Bullies’ from their aggressive style, which utilized fighting and physical play as a feature of their game plan. 

Philly’s bullies famously played against the Russian national team in an exhibition game in 1976, where the ‘Red Army’ team left the ice in protest after a body check from Flyers’ defenseman Ed Van Impe. The game was a part of a series of matchups between the Red Army team and NHL teams, and the Flyers’ 4-1 win was the only time the Russians lost that year. 

Since the 70s, Philly has had numerous chances in the Stanley Cup Finals but hasn’t come away with the Cup. The Flyers have appeared in six Finals since 1975, losing in each one. 

The most recent chance came in 2010 when the team, led by Claude Giroux, Chris Pronger, and Danny Briere, lost in six games to the Blackhawks. 

This past year, Philly defeated their blood rival, Pittsburgh, to advance to the second round, where it lost in four games to Carolina. The Flyers have +5000 odds to win the Stanley Cup this season. 

3. Vancouver Canucks, 55 seasons

The Canucks have never won the Stanley Cup in their 55 seasons as a franchise, but they’ve come very close a couple of times.

Many teams across all professional sports have a history of tough playoff losses, and many teams have lost in the championship game a couple of times. No fanbase, however, has had a more infamous reaction to losing in a championship series than Vancouver fans. 

The Canucks have lost in Game 7 of the Stanley Cup Finals twice, first in 1994 and then again in 2011. Both times, the citizens of Vancouver have basically destroyed their city. 

The 1994 riot, which followed a loss to the Rangers in New York, had some insane figures: 200 injuries, 50 arrests, and $1.1 million in property damage, which equates to $2.14 million in 2026. The fact that the game was on the road dampened the fallout somewhat. 

They say the sequel isn’t better than the original, but the 2011 riot broke that rule. As soon as the Bruins finished off a 4-0 Game 7 win at Rogers Arena, rioting broke out once again. This one caused $4 million in property damage, estimated to be $5.5 million in 2026, along with 140 injuries, 301 arrests, and 1,204 criminal charges. 

This riot ended outdoor watch parties in the city of Vancouver. 

The Canucks finished with the league’s worst record last season and have the longest Stanley Cup odds for this upcoming season at +50000. 

2. Buffalo Sabres, 55 seasons

Buffalo, which entered the NHL at the same time as Vancouver, has also never won the Stanley Cup. 

The Sabres have compiled over 2,000 wins across their time as a franchise, but have never won the biggest prize in hockey. They’ve appeared in the Finals twice, in 1975 and in 1999. They lost both series in six games. 

Their 1999 Finals loss is infamous. The series-ending goal, which came from Dallas’ Brett Hull in the third overtime of Game 6, appeared to happen when Hull’s left skate was inside the crease. Upon review of the goal, the league said that it was good, but Buffalo fans continue to question whether it should have been overturned. 

Prior to this past year, the Sabres had the league’s longest playoff drought at 14 seasons. They broke that and advanced to the conference semifinals, where they lost to the Canadiens in seven games.

Ahead of the 2026-27 season, Buffalo has the 12th-best odds to win the Stanley Cup, currently set at +2800. 

While they’re in a crowded division inside of a competitive conference, with a few improvements, the Sabres should be viewed as a contender for the Stanley Cup next season. 

1. Toronto Maple Leafs, 59 seasons

One of the league’s most iconic franchises hasn’t won a Stanley Cup in almost 60 years. 

With the New York Knicks winning the NBA Finals this year, you could make the argument that Toronto owns the last great title drought in North American professional sports. 

The last time the Maple Leafs won the Cup was in 1967, and they have not appeared in a Finals since then. Despite that ginormous gap between titles, Toronto still has the second-most championships in the NHL with 13. 

Their most recent run — with their ‘Core Four’ of Auston Matthews, John Tavares, William Nylander, and Mitch Marner — looked like the best chance they’ve had in a while to break that drought, but the team still fell short. 

The Maple Leafs have not appeared in a Conference Finals since 2002, when they lost to the Hurricanes in six games. 

After Marner’s exit last summer, Toronto had a disappointing 2025-26 season, missing the playoffs. For their one year of struggle, the hockey gods handed them the first overall pick and the opportunity to select Gavin McKenna, who looks to be a generational forward prospect. 

Maybe McKenna can be the one piece to ultimately put the Maple Leafs over the top. 

But as far as next season goes, Toronto is a bit of a long shot to win the Cup with +3500 odds.