Stanley Cup Droughts: 5 Teams Who’ve Been Waiting the Longest For Another Title

In just a few short weeks, a new champion in the NHL will be crowned, and one of the final four contenders has waited decades for the chance to win back Lord Stanley’s Cup.

The last time the Edmonton Oilers won the Stanley Cup was in 1990, when they defeated the Boston Bruins in five games, despite the absence of Wayne Gretzky, who had been traded to Los Angeles in the summer of 1988. 

While Connor McDavid may lead the Oilers back to a Stanley Cup win this June, four other teams who have been waiting even longer will not have a chance to win the Cup. 

What follows are the four longest Stanley Cup droughts still going in the NHL. 

Please note that teams that have never won the Cup are not included in this list, which makes perfect sense to me. You’d never say it’s been 20 years since you’ve eaten a hot dog if you’d never eaten a hot dog before. 

1. Toronto Maple Leafs

I thought the Maple Leafs had a chance to end their drought this season, but it’ll be another year in waiting for the fans who haven’t seen a Cup in 57 years. 

The last time the Stanley Cup was won in Toronto was in 1967. For reference, in that year, the NHL still had only six teams, we were still two years away from the Moon landing, McDonald’s introduced the Big Mac, and Wayne Gretzky was six years old. 

The ‘67 title was the 13th for the Maple Leafs and featured the oldest lineup of players ever to win the Cup, with an average age of 31. 

Toronto defeated the Chicago Blackhawks in six games and then went on to beat the Canadiens in the Finals, also in six games. 

Since then, the Maple Leafs have never returned to the Stanley Cup Finals despite five appearances in the Conference Finals. The closest they got was in 1993 when they faced the Gretzky-led Kings. They lost 5-4 at home in Game 7 at the hands of a Gretzky hat trick. 

Toronto had a solid chance to win the Cup in recent years with its star-studded ‘Core Four’ of Auston Matthews, Mitch Marner, John Tavares, and William Nylander. But with Marner likely to leave this offseason, the window of contention for that group may be shut. 

2. Philadelphia Flyers

Philadelphia’s last Stanley Cup came 49 seasons ago in 1975 during the famed Broad Street Bullies era of the team. 

1975 was the second of the back-to-back titles for the Flyers, the only two championships in franchise history. Philadelphia advanced to the Finals after sweeping the Maple Leafs in the first round and then beating the Islanders in seven games. 

The ‘75 Finals, where the Flyers met the Buffalo Sabres, was the first played between two non-Original Six teams. Philadelphia won the series in six games. 

The series is also famous for Game 3 in Buffalo, where the game was delayed twice due to fog in the arena and a bat flying above the crowd. Sabres center Jim Lorentz killed the bat with his stick, earning him the nickname Batman from teammates, and arena employees skated around the ice waving bed sheets to lessen the fog. 

Since then, the Flyers have returned to the Finals six more times, most recently in 2010. 

Now the team is in a prolonged state of rebuilding, having missed the playoffs in five straight years and seven of their last 10 seasons. 

Philadelphia recently made a coaching change, though, swapping out John Tortorella for Flyers Hall of Famer and former Vancouver Canucks head coach Rick Tocchet. 

3. New York Islanders

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

The Islanders ripped off four straight in the late 1970s and early 1980s, the only championships in their team’s history. 

New York arrived at the Finals after defeating the Capitals in five games, the Rangers in six, and the Bruins in six in the previous rounds. In the Finals, they met the Edmonton Oilers, their first appearance in the championship series as a franchise. 

The Islanders won the series in a dominant sweep with an impressive performance from the Conn Smythe-winner, goaltender Billy Smith. Smith had a 2.68 GAA and a .912 save percentage in those playoffs, the highlight of which came when he shut out the legendary Gretzky-led Oilers scoring group. 

No team in North American professional sports has won four consecutive titles since this New York team did it. 

But since the dynasty in the 1970s and 1980s, there hasn’t been much else to celebrate for Islanders fans. They lost in the Stanley Cup Finals the following year in a rematch against Edmonton. Following the 1987 season, the team went two decades without winning a playoff series. 

They underwent an ugly rebrand in the 1990s, which fans hated. They were almost purchased by a Dallas businessman named John Spano, who turned out to be pretending to be much wealthier than he was and subsequently spent time in prison on fraud charges related to his attempted purchase. 

The team also briefly relocated to Brooklyn’s Barclays Center in the 2010s, an arena specifically designed for basketball, before building a new arena on Long Island. 

New York has the number one pick in the upcoming draft, but they’re still a long way away from being close to contention again. 

4. Calgary Flames

Last on our list, with the four longest Stanley Cup drought, is the Calgary Flames, who haven’t won since 1989. 

It’s inarguably the apex of the Flames franchise, given that it’s their first and only championship in team history. That same year, they were also division champions (their second of three division titles) and Presidents’ Trophy champions (their second and most recent win). 

Perhaps this title requires an asterisk because Calgary was able to advance to the Cup Finals mainly because their biggest rival and conference threat that season, the Oilers, were eliminated in the first round by the Los Angeles Kings. 

They won their opening round series against Canucks in seven games, then beat the Kings in a sweep, and advanced to the Finals after Chicago in the Conference Finals in six games. 

They then met the Montreal Canadiens, in the most recent meeting of two Canadian teams in the Stanley Cup Finals, and won the series in six games. 

After that title, the Flames did not win a playoff series again until the 2003 season, when they returned to the Stanley Cup Finals and lost to the Tampa Bay Lightning. Since then, they’ve only made it past the first round of the playoffs twice. 

This also allows me to discuss the incredibly strange and stacked Calgary teams of the late 2010s and early 2020s, who inexplicably failed to make any significant noise in the playoffs. 

The teams featured the late great Johnny Gaudreau as the star alongside one of the current faces of the NHL, Matthew Tkachuk. The teams were invariably rounded out by some combination of Sam Bennett, Elias Lindholm, Noah Hanifin, Nikita Zadorov, and Chris Tanev. 

If you’re a Flames fan you’re painfully aware of this, and I’m sorry for rubbing salt in the wound, but it’s just one of the strangest situations in recent NHL memory.