It’s often said that the Stanley Cup is the hardest trophy to win in professional sports. Of the league’s 32 teams, only 20 have won the Stanley Cup and just 14 have won multiple championships. In the modern era, it’s become tougher to win championships and build dynasties which begs the question: what are the longest active Stanley Cup droughts?

Dating back to the original expansion year of the NHL, there are 11 active teams that haven’t won a Stanley Cup since their inception. The record for the longest drought ever goes to the Toronto Maple Leafs, currently sitting at 55 years since their Cup win in 1967.

Related: 11 NHL Teams Without a Stanley Cup

Numerous teams in recent memory have ended their Cup drought. The Chicago Blackhawks went 47 years before winning the Cup in 2010, and the Los Angeles Kings went 43 seasons prior to their 2012 win. The Washington Capitals were on this list before Alex Ovechkin and the team won their first championship in the team’s history in 2018. They went 43 years without winning the ultimate trophy before that. In 2019, the St. Louis Blues got to take their name off of this list after 51 years of never winning a Cup.

Here is a list of the longest Cup droughts, with several notable teams and a few that have come agonizingly close on multiple occasions.

5. Arizona Coyotes

Length of Drought: 44 Years

Originally coming into the league as the Winnipeg Jets in 1979, the Arizona Coyotes are one of those 11 teams to never win the Stanley Cup. They relocated to Phoenix as the Phoenix Coyotes in 1996, and then in 2014 changed the name to the Arizona Coyotes. No matter their location or name though, the team has never even reached the Stanley Cup Final.

Their closest encounter came in the 2011-12 season, the only trip in franchise history to the conference final. They had just won the franchise’s first-ever division title and were heading into the playoffs with home ice. In Round 1, they defeated the strong Blackhawks in six games, their first series win since 1987. They then defeated the Nashville Predators in five games to reach the third round and the Kings.

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While they had a great run, the team fell in five games to the eventual Cup champions (who ended their 43-year drought in the process). Goaltender Mike Smith was the main reason the team went as far as they did, posting a 1.99 goals-against average and a .944 save percentage.

Despite having some amazing players through the years like Teemu Selanne, Bobby Hull, Phil Housley, Keith Tkachuk, Shane Doan and Jeremy Roenick, the team has yet to really contend for the Cup.

4. Philadephia Flyers

Length of Drought: 48 Years

The Philadelphia Flyers joined the league in 1967 and took just seven years to win their first Stanley Cup. That was in 1973-74 and they didn’t waste any time with their second, winning it again the following season. This was the most famous era in Flyers history, with the Bobby Clarke-led Broad Street Bullies terrorizing the league. Having Bernie Parent in net didn’t hurt either who, along with the Cup, won the Vezina Trophy and the Conn Smythe Trophy in both seasons.

Since their back-to-back Cup wins, the Flyers have had their chances. The season after their second title they were back in the Final when they were swept by the Montreal Canadiens. Since then, they’ve been to the Cup Final six times, most recently in 2009-10 when they fell to the Chicago Blackhawks, losing in overtime of Game 6. In that run, they joined a legendary list of sports teams to overcome a 3-0 playoff deficit and win the series in the Conference Semifinals versus the Boston Bruins.

The Flyers have had tremendous talent since their back-to-back Stanley Cups, from Eric Lindros to Marc Recchi to Mark Howe. Even now they have some of the best players in the league, including Claude Giroux and Sean Couturier, but haven’t been able to get past the first round since 2011-12, not even making the playoffs every other season since.

T-2. Vancouver Canucks

Length of Drought: 52 Years

The Vancouver Canucks have come awfully close on a few occasions. There were two Cinderella runs in 1982 and 1994, both against New York teams. They lost the first against the Islanders during their dynasty years despite the goaltending heroics of “King” Richard Brodeur. They then came agonizingly close in a heartbreaking Game 7 defeat against the Rangers in 1994.

That 1994 Canucks team led by Trevor Linden, Pavel Bure, and Kirk McLean might’ve been the most beloved team in franchise history, but it was the 2011 team that arguably hurt the most. Led by the Sedin Twins, Ryan Kesler, and Roberto Luongo, the Canucks exorcised their playoff demons against the Chicago Blackhawks before running into a wall against the big bad Bruins.

There was the infamous riot that ensued and shut down the downtown core of the city, and the Canucks haven’t come close since. After going through some turmoil and roster turnover, the Canucks have rebuilt and are back into contention. Elias Pettersson, Brock Boeser, and Quinn Hughes will be very much a part of that.

T-2. Buffalo Sabres

Length of Drought: 52 Years

After joining the league in 1970-71 alongside the Canucks, the Buffalo Sabres took just four seasons to make it to the Stanley Cup Final. They did that in 1975 against the Flyers during their Broad Street Bullies era. The Sabres weren’t to be outdone with their French Connection trio of Gilbert Perreault, Rene Robert and Rick Martin, but the Flyers were just too deep for the Cinderella Sabres who lost in six games.

The Sabres made another miraculous run to the 1999 Cup Final on the back of Dominik Hasek during the height of his league dominance. Despite all the magical stories from that spring, the only thing people still talk about is Brett Hull’s controversial foot in the crease goal that won the series in overtime.

After the 2005-06 lockout, the Sabres took off and looked poised to win their first Stanley Cup with an offensively gifted and deep roster led by Chris Drury, Daniel Briere and Ryan Miller in goal. They lost in back-to-back Conference Finals in 2006 and 2007, with the loss to the Carolina Hurricanes in 2006 going seven games.

The future is bright in Buffalo. If they contend soon, it’ll be Rasmus Dahlin who will hopefully bring the franchise their first Stanley Cup.

1. Toronto Maple Leafs

Length of Drought: 56 Years

The Leafs are one of the most storied franchises in the NHL since joining the league in 1917. The Leafs have the second most Stanley Cup championships in league history behind the Canadiens (24) with 13 titles. The last came in 1966-67 when Toronto faced off against their arch-rivals from Montreal in a thrilling six-game series. Dave Keon was named just the third Conn Smythe Trophy winner in league history, and it capped off a remarkable four Stanley Cups in six years.

Since then the Leafs have gone through an agonizing stretch from trading Frank Mahovolich a year after winning the Cup, or the Harold Ballard years to that controversial Gretzky high stick on Doug Gilmour during the 1993 Playoffs. The Leafs have come close a few times but haven’t made it past the Conference Final since their 2002 loss to the Hurricanes.

Luckily for Toronto fans, with a core of Auston Matthews, John Tavares, Morgan Rielly and Mitch Marner, the team has a real shot to end the drought in the near future.

Complete List of Stanley Cup Droughts

Here’s the complete 31-team list of Stanley Cup droughts in alphabetical order:

NOTES

Team Notes:

* The Arizona Coyotes were formerly the original Winnipeg Jets and became the Coyotes in 1995-96, so their streak is from when the Jets joined the NHL in 1979.

** The Minnesota Wild are a separate franchise than the former Minnesota North Stars. The North Stars moved to Dallas in 1993-94, winning the Stanley Cup in 1999.

*** Then there are the new Winnipeg Jets who were formerly the Atlanta Thrashers. The Thrashers joined the NHL in 1999-2000 and that franchise relocated to Winnipeg for the 2011-12 season.