Teams With Longest Stanley Cup Droughts Led By Maple Leafs

Seeing your team win a Stanley Cup is the ultimate reward for being a loyal fan. 

However, some teams are rarely among the Stanley Cup odds favourites at the BetMGM online sportsbook.

Others haven’t won a Cup in a generation, continuously testing their fans’ devotion with each passing season.

Just imagine how sweet success will taste when, or should I say if, it finally comes around. Here are the teams enduring the longest Stanley Cup droughts.

Which NHL Teams Have Gone the Longest Without Winning the Stanley Cup?

7. Calgary Flames (1989, 37 years) 

The Calgary Flames have one Stanley Cup banner hanging from the rafters, and it came in 1989, with a 4-2 series win in the final over the Montreal Canadiens. Al MacInnis won the Conn Smythe Trophy, and Mike Vernon backstopped the team to glory. 

The Flames have been in three Stanley Cup Finals, losing in 1986 to the Canadiens and in 2004 to the Tampa Bay Lightning. 

The Flames are also among the teams with the longest NHL playoff droughts.

6. New York Islanders (1983, 43 years) 

It’s feast or famine for the New York Islanders, who haven’t won the Stanley Cup in 43 years. 

Before their drought began, the Islanders lost to the Edmonton Oilers in the Stanley Cup Final. That followed the franchise’s four consecutive Stanley Cups. The Islanders are the last NHL team to win more than two Cups in a row, so don’t feel too bad for the fan base. 

5. Winnipeg Jets/Arizona Coyotes/Utah Mammoth (never, 46 years)

No matter the location, this franchise has never advanced to a Stanley Cup Final, let alone win a championship. 

The Utah Mammoth made the playoffs in the second season after relocating from Arizona. Utah hopes a better fate befalls their team than those which wobbled along in Arizona and Winnipeg. 

The best run came while the team was in Arizona, when it lost in the 2012 conference final to the eventual Stanley Cup champion, the Los Angeles Kings. 

4. Philadelphia Flyers (1975, 50 years)

After seven seasons in the league, the Philadelphia Flyers won back-to-back Stanley Cups. They beat the Boston Bruins and Buffalo Sabres in the 1974 and 1975 Stanley Cup Finals, respectively. 

While they haven’t won the Cup since, it hasn’t been from lack of opportunities. The Flyers have advanced to six Stanley Cup Finals since, the last of which, in 2010, ended in a six-game defeat to the Chicago Blackhawks. 

3. Buffalo Sabres (Never, 55 years)

You have to feel for Sabres fans, who have never seen their team win a Stanley Cup despite being around for 55 seasons. 

Not only has the team endured the third-longest barren patch, but it also failed to make the playoffs for 15 years before securing a berth in 2026. 

They entered the league in 1971 and made the Stanley Cup Final four seasons later, losing to the Flyers. 

The Sabres got back to the Stanley Cup Final in 1999, but lost in six games to the Dallas Stars. 

2. Vancouver Canucks (Never, 56 years)

It took the Vancouver Canucks 11 years to reach the Stanley Cup Final, only to be swept by the Islanders in 1982.

Twelve years later, they faced the New York Rangers in their second Stanley Cup Final. While it went down to the wire, the Canucks lost 3-2 in Game 7.

Their most recent trip to the showcase final ended in heartbreak yet again, this time falling to the Boston Bruins in 2010 after winning the first two games at home.

1. Toronto Maple Leafs (1967, 59 years)

The Toronto Maple Leafs haven’t made a Stanley Cup Final since their last championship in 1967. That’s 59 years of disappointment. 

From 2004 to 2022, the Maple Leafs failed to advance past the first round of the playoffs, a span of 17 seasons. 

They made it to the conference final four times since 1967, the last in 1999, when they lost in five games to the Sabres.

When Was the Last Time a Canadian Team Won the Stanley Cup?

The Montreal Canadiens won the Cup in 1993, the last time a Canadian team reigned supreme. 

Which NHL Teams Have Never Made a Stanley Cup Final? 

The Mammoth, Jets, Blue Jackets, and Wild have never made a Stanley Cup Final.