The NHL's 7 Most Painful Stanley Cup Droughts

The Carolina Hurricanes are facing the Vegas Golden Knights in the Stanley Cup Final. While the Golden Knights hoisted the Stanley Cup in 2023, Hurricanes fans have been waiting much longer - 20 years to be exact.

That’s nothing. Imagine being a Toronto Maple Leafs fan still dealing with a 59-year championship drought. We’re talking about a Canadian franchise that has won 13 Stanley Cup titles, but the most recent crowning moment took place in 1967. 

Do you know the last time a Canadian team won the Stanley Cup? That honor belongs to the 1993 Montreal Canadiens.  

Believe it or not, there are franchises, including two that qualified for this year’s Stanley Cup Playoffs, that are still trying to win the first one. 

Using the teams from this year’s playoff bracket, we’re going to highlight seven squads stuck in what seems like a never-ending championship drought. 

Stanley Cup Final: Golden Knights Vs. Hurricanes 

If we go back to last June, the top NHL betting sites had the Carolina Hurricanes listed among the favorites to win the 2026 Stanley Cup. Early DraftKings Sportsbook odds had the Eastern Conference champions priced at +900, which was right in line with the Colorado Avalanche and Dallas Stars. The Edmonton Oilers (+650) and defending champion Florida Panthers (+700) were the top two teams on the board.

The Golden Knights had +1200 odds of winning the Stanley Cup.

Carolina entered Game 1 of the Stanley Cup Final (-155) as a slight favorite over Vegas (+130).   

Criteria for Stanley Cup Championship drought list 

Instead of looking at all 32 NHL clubs, to be considered for the Stanley Cup championship drought list, the team at the very least had to qualify for this year’s NHL Playoffs. The Hurricanes automatically made the list, being that they’re one of the last two teams standing and have not won since 2006. Based on this, we picked seven teams that are currently experiencing a championship drought of two decades or longer. 

The Golden Knights weren't even considered since there was a Stanley Cup championship parade on the Las Vegas Strip three years ago. 

7 NHL Teams Looking To End Stanley Cup Void

Buffalo Sabres 

Last championship: Still waiting 

Sabres fans have it tough. Since joining the league in the 1970-71 season, the Buffalo Sabres have never won a Stanley Cup title. Sure, they have gotten close two times in 1975 and 1999, but lately, just making the postseason cut has been a challenge. By making it this season, the franchise no longer has to talk about extending that dreaded league record of 14 seasons of playoff futility.

While this year’s chapter has come to a close, Buffalo did advance to the Eastern Conference semifinals, which went seven games.    

For now, the Sabres' hockey championship drought is at 55 seasons and counting.

Philadelphia Flyers 

Last championship: 1975

Flyers fans have been waiting five decades for a parade down Broad Street. Getting back to the Eastern Conference Final has been a challenge, as the last time that happened was 2010. That year, Philadelphia lost to the Chicago Blackhawks in the Stanley Cup Final. It ended a 49-year championship drought for Chicago. 

The Flyers did take a giant leap forward this season, ending a postseason drought that dated back to 2019-20. However, instead of just making it this season, Philadelphia took things a step further by defeating the Pittsburgh Penguins in six games. The team might not have won any games against Carolina, but two were decided in overtime.   

Carolina Hurricanes

Last championship: 2006

When looking at this year’s Stanley Cup Playoff bracket, it’s hard not to notice how dominating the Carolina Hurricanes have been. The team entered the Stanley Cup Final 12-1 overall, which included series sweeps over the Senators and Flyers. After dropping Game 1 of the Eastern Conference Final to Montreal, Carolina won the next four.

So is this the year that the Cup finally finds its way back to the Tar Heel State? The Hurricanes were the Eastern Conference’s top team during the regular season with a 53-22-7 record. 

Head coach Rod Brind’Amour served as Carolina’s team captain during the 2006 championship season. He became the team’s head coach before the 2018-19 season.  

Montreal Canadiens 

Last championship: 1993 

Yes, it has been more than three decades since the Canadians have been able to call themselves NHL champs. We’re talking about an Original Six franchise that has won the most Stanley Cups in league history with 24. 

Winning hockey’s top prize is the ultimate goal, but making it to the conference final shows signs of hope, as the team was eliminated in the first round in 2025 and missed the playoffs completely the previous three seasons. Montreal did make the 2021 Stanley Cup Final, but lost to the Tampa Bay Lightning.  

Edmonton Oilers 

Last championship:1990

Out of all of the teams included on this list, the Edmonton Oilers have come the closest without winning it all. The team made the 2024 and 2025 Stanley Cup Finals, losing to the Florida Panthers both times. As long as generational talent Connor McDavid is on the roster, the Oilers have a very good chance of being in the championship conversation. Edmonton was the preseason favorite to win it all. 

The last Oilers team to raise Lord Stanley’s Cup was absolutely stacked with Mark Messier, Jari Kurri, and Glenn Anderson. 

This time around, Edmonton failed to make it out of the first round.

Ottawa Senators

Last championship: Never

This version of the Ottawa Senators, not the one that was part of the Original Six, has yet to win hockey’s top prize. Since joining the league as an expansion team during the 1992-93 season, the Senators have advanced to the Stanley Cup Final just once. That would be the 2006-07 season when the Anaheim Ducks won in five games.

The Senators have made the postseason in back-to-back seasons, losing in the first round both times. It includes getting swept by the Carolina Hurricanes.     

Dallas Stars 

Last championship: 1999

The Dallas Stars have come close in recent seasons to stopping the chatter about the lack of championships. The only one in franchise history happened way back in 1999. Dallas did play in three straight Western Conference Finals between 2023 and 2025. The team enjoyed a solid regular season with a 50-20-12 record for 112 points - the third most among NHL clubs. 

Once the postseason rolled around, the Stars ran into a talented Minnesota Wild team that won the series in six games. Some might call this season a step backward, but the Stars are still one of the league’s top teams. Right now, the first step is figuring out how to make the Stanley Cup Final for the first time since 2020.  

Waiting decades for a championship is not uncommon

While the NHL is front and center right now due to the Stanley Cup Final getting the national spotlight, every pro sport has similar situations. Looking at the NFL, the Buffalo Bills have been in the league since 1970 and played in four Super Bowls. Do you know how many times the team has lifted the Vince Lombardi trophy in the air?

Try zero. 

Looking at this year’s NBA Finals matchup between the Knicks and Spurs, New York’s last NBA championship came in 1973.

Depending on which team you’re rooting for, these long and drawn-out championship droughts can deliver nothing but heartache. If and when your favorite team finally wins it all, the painful memories associated with decades of coming up short are immediately cured.