Longest Cup Droughts
The modern-day Senators — not the same franchise as the one which won 11 Stanley Cups in the early 20th century — have been in the NHL since the 1992-93 season and have been searching for their first title since then. Their one and only trip to the Finals came in 2006-07, when they knocked off the top three seeds in the Eastern Conference and met the Anaheim Ducks. The Ducks rolled over Ottawa in five games en route to their first NHL title ever.
The Sharks joined the NHL one season before the Senators, and have yet to even make it to the Cup Finals. The closest they’ve come was in 2003-04, when they lost the Western Conference Finals in six games to the Calgary Flames.
It’s hard to imagine now, but once upon a time the Oilers were a nearly unstoppable force in hockey. They won five Stanley Cups in the 1980s, but have largely struggled just to make the playoffs since the early ’90s. Other than the dream season of 2005-06 — when the Oilers took the Carolina Hurricanes to the seventh game of the Cup Finals — Edmonton has typically either failed to qualify for the postseason or been eliminated in the first round.
I vaguely remember the Flames’ Cup-winning 1988-89 campaign, and that goaltender Mike Vernon was really good. But after beating the Canadiens in six games for their only title to date, it’s been a bit of a slog for Calgary. They failed to make the playoffs for seven straight seasons (1996-97 through 2002-03), but then made a miracle run through the playoffs in 2003-04, losing the Cup finals in seven to the Tampa Bay Lightning. That run also contained the only playoff series wins for the franchise since 1989. Ouch.
It’s hard to picture, but there was a time when Islanders fans could legitimately rag on New York Rangers fans for their lack of titles. The chants of “1940!” still ring loudly in my memory to this day. But that was a loooong time ago, and the Islanders have simply been one of the worst teams in hockey over the last few decades. New York’s last playoff series win came against Pittsburgh in 1993.
Of the teams on this list, only two have never even been to the Stanley Cup finals. San Jose is one and Phoenix/Winnipeg is the other. The Coyotes have yet to advance past the Western Conference quarterfinal round.
It’s certainly not is if the Flyers haven’t had ample opportunity to follow up on their championship season of 1974-75 — they’ve advanced to the Finals six times since then. They’ve also only missed the playoffs six times in the last 35 campaigns, a damn remarkable record of consistency. The Flyers have just been able to seal the deal for some reason, most recently losing the Finals in six games to the Chicago Blackhawks in 2010.
The Capitals have turned in a collection of largely respectable regular seasons after a rough start to their NHL life in 1974-75 (they failed to qualify for the playoffs in their first eight years). But in terms of the playoffs, Washington’s been stuck in second gear. The two exceptions to this were in 1989-90 — when they got blanked by Boston in the Eastern Conference Finals — and their Cinderella run in 1997-98. That year the Caps cruised over Ottawa and won a pair of dramatic series against Boston and Buffalo before getting steamrolled in the Finals by the Detroit Red Wings.
Buffalo and Vancouver are together at the #2 spot by virtue of neither team having won a title since they both entered the league in 1970-71. The Sabres and Canucks have five Finals appearances between them, with Vancouver coming the closest to winning. The Canucks took both the Rangers (1994) and Bruins (2011) to seven games, and in both cases the citizens of Vancouver took the losses pretty hard.
So what’s worse — to root for a team that has never won a title in their entire four-plus decade existence, or to root for a franchise that was once one of the NHL’s greatest but hasn’t hoisted the Stanley Cup since the Original Six era? Being a Devils fan I can’t really say, but it sure seems like Toronto fans are taking the Maple Leafs’ futility hard. Not only have they not won it all since 1966-67, that’s also the last year they even made it to the Finals. The Blues have fared little better, never winning a title and not making it to the Finals since 1969-70, the last of three consecutive trips. The Los Angeles Kings, meanwhile, never did get a Cup while having Wayne Gretzky in silver and black.