The 10 Longest Stanley Cup Droughts In NHL History

There isn’t a single trophy up for grabs in the world of sports that’s more iconic than the Stanley Cup, and the NHL teams who compete for it have to endure a grueling battle if they want to hoist it. Getting to the mountain top is certainly no small feat, and there are a number of franchises that have spent decades trying (and failing) to arrive there.

Any sports fan who hitches their wagon to a team does so knowing they’re going to deal with plenty of ups and downs, and when you’re forced to endure the lowest lows, it can make the rush that comes with seeing them win a championship feel even better.

Unfortunately, there are plenty of fan bases that have been forced to endure a very lengthy wait due to their team’s struggles to secure a title—including those of the NHL teams responsible for the longest Stanley Cup droughts in the history of the league.

Toronto Maple Leafs: 57 Seasons

The Maple Leafs headed into the postseason in 2025 hoping to end what is both the longest active Stanley Cup drought in NHL history and the longest one any franchise has dealt with at any point, but they came up short yet again with a loss to the Panthers in the second round.

The Maple Leafs have the second-most titles of any NHL team at 13 (the Canadiens firmly lead the pack with 23), but most of their fans weren’t even alive to witness their most “recent” Stanley Cup victory in 1967.

Toronto hasn’t even made the final round since then; they did make four trips to the conference final between 1993 and 2002, but that’s the closest they’ve come in nearly six decades.

Buffalo Sabres: 54 Seasons

The Buffalo Sabres missed the playoffs for the 14th straight year this season to extend the longest postseason drought in NHL history, and that obviously has not done wonders when it comes to their quest to end a Stanley Cup drought that stretches back to the franchise’s inception in 1970.

The Sabres do have two Stanley Cup appearances to their name: they lost to the Flyers in six games during their first one in 1975 and fell to the Stars in the same fashion in 1999.

However, based on the current state of the franchise, the pain isn’t going to come to an end at any point in the near future.

Vancouver Canucks: 53 Seasons

The Canucks joined the NHL the same year as the Sabres, and they’ve also been unable to win a Stanley Cup since entering the league.

It took Vancouver a bit longer to make it to its first Stanley Cup Final, and they were swept by the Blackhawks after checking that box in 1982.

They fell into a 3-1 hole against the Rangers in their championship showdown in 1994 before New York put things away in seven games, and while they had two opportunities to put the Bruins away in 2011, Boston clinched the series in the city that proceeded to riot in the wake of that Game 7 loss.

New York Rangers: 53 Seasons

Speaking of the Rangers…

This is the first drought on this list that isn’t an active one (although New York has now gone more than three decades without winning the Stanley Cup).

As was the case with the Maple Leafs, the Rangers were an Original Six team, but they were only able to rack up a handful of championships during the NHL’s early days before winning their third in 1930.

They subsequently had three Stanley Cup Final appearances where they came up short before finally getting over the hump at the expense of the Canucks with the aforementioned victory in 1994.

St. Louis Blues: 50 Seasons

The NHL welcomed the Blues into the fold in 1967, and the franchise arrived with a bang by making the Stanley Cup Finals in each of its first three seasons.

Unfortunately, those first two appearances ended with them being swept by the Canadiens, and they befell the same fate when they met the Bruins in 1970.

It took close to five decades, but St. Louis got a rematch with Boston in its first Stanley Cup Finals appearances since Bobby Orr scored the most iconic goal in NHL history and brought the drought to an end by winning in seven games.

Philadelphia Flyers: 49 Seasons

The Flyers also joined the NHL in 1967, and while it took them a little longer to make it to the Stanley Cup Final for the first time, they took full advantage by winning the first of back-to-back championships in 1974 (which came at the expense of the Bruins and the Sabres).

However, the franchise has been hunting for its third Stanley Cup ever since and is currently riding a six-game losing streak in the final, with the most recent defeat coming at the hands of the Blackhawks in 2010 courtesy of one of the weirdest title-clinching goals ever scored.

Chicago Blackhawks: 47 Seasons

That aforementioned goal may have left Flyers fans equal parts confused and disappointed, but it was an absolutely massive tally for a Blackhawks franchise that had spent close to 50 years attempting to return to glory.

As was the case with the Rangers, the Blackhawks were an Original Six team that underachieved based on how many titles the other members of that club were able to rack up in the early days of the league; they won the Stanley Cup twice in the 1930s before getting it a third time in 1961.

Chicago made it to the finals four times in the next 12 seasons but came up short every time, and they had to wait until 2010 to return before finally getting their fourth title (they added two more with wins in 2013 and 2015).

 

Arizona Coyotes: 44 Seasons

This one requires some background, as this drought encompasses the entire existence of the franchise that began as the Winnipeg Jets in 1979 (which is a separate entity from the Winnipeg Jets that have not won the Stanley Cup since being reincarnated in 2011 and have a drought stretching over 25 seasons if you account for their time as the Atlanta Trashers).

With that history lesson out of the way, neither the (original) Jets nor the Coyotes were able to win a Stanley Cup or even make it to the finals before the franchise folded in 2024.

Los Angeles Kings: 43 Seasons

The Kings are the third team on this list to join the NHL in 1967, and it took them much, much longer to find their footing compared to the Blues and the Flyers.

Los Angeles didn’t make it to the Stanley Cup Final for the first time until 1993 after getting a little bit of help from a guy named Wayne Gretzky. Unfortunately, The Great One could only do so much in a showdown where the Canadiens clinched the series in five games.

The franchise had to wait close to two decades to get another shot and was able to end the drought by beating the Devils in six games in 2012.

Washington Capitals: 42 Seasons

We’re capping things off with the Capitals, who played their inaugural season in 1974 but had to wait until 1998 for their first Stanley Cup Finals appearance (a sweep at the hands of the Red Wings).

Alex Ovechkin eventually breathed some new life into a franchise that had to deal with a string of disappointing playoff exits before finally returning to the finals in 2018, and Washington prevented the Golden Knights from capping off their first season of existence with a Stanley Cup by winning in five games.