The National Hockey League gets a bad rep for allowing so many teams to qualify for the playoffs, but the thing is this — it’s still really, really hard to make it through the playoffs and all the way to a Stanley Cup title. That’s especially true for these ten franchises, each of which has not taken home Lord Stanley’s trophy in a long, long time (some of them never). The season drought totals below are correct as of the start of the NHL’s 2014-15 Stanley Cup playoffs. (See also: The 10 longest title droughts in NBA history.)

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#10. San Jose Sharks (22 seasons)

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.

#9. Edmonton Oilers (23 seasons)

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. Still, their achievements during their heyday are still enough to earn them a spot in my list of the top 10 NHL franchises ever.

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. The 2012-13 season marked the seventh consecutive campaign without a trip to the playoffs for the Oilers, the longest active streak in hockey.

#8. Calgary Flames (24 seasons)

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.

#7. New York Islanders (30 seasons)

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.

To put that in perspective, consider the following about that season — the Atlantic Division was still known as the Patrick Division, the NHL added its 23rd and 24th teams (Ottawa and Tampa Bay), and there were still franchises in Quebec and Hartford.

Despite actually making the postseason last season for the first time since 2006-07, it seems unlikely that the Long Island faithful will witness a return to glory before the Islanders make the move to Brooklyn.

#6. Phoenix Coyotes/Winnipeg Jets (34 seasons)

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. Oh sure, the Jets — the original version mind you, not the relocated Atlanta Thrashers — won the WHA championship three times in the ’70s. But that momentum was lost when Winnipeg joined the NHL in 1979-80, and the franchise seemingly hasn’t ever recovered. The team’s last playoff series win was as the old Jets in 1987. In fact, that series win over Calgary was the second of just two for the franchise ever.

The Coyotes have yet to advance past the Western Conference quarterfinal round. They currently occupy the #3 spot on my lost of the worst NHL franchises of all-time.

#5. Philadelphia Flyers (38 seasons)

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 nine times in their entire history, 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. They are easily the best franchise in hockey to go so long without a Cup.

#4. Washington Capitals (39 seasons)

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 for about 15 years.

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.

Caps fans still hope that superstar captain Alexander Ovechkin can lead Washington to Cup glory, but thus far the team has just two playoff series wins during his tenure.

#3 (tie). Buffalo Sabres and Vancouver Canucks (43 seasons)

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 the Rangers (1994) and Bruins (2011) to seven games, and in both cases the citizens of Vancouver took the losses pretty hard.

The Sabres, meanwhile, haven’t even won a playoff series since they bested the New York Rangers in the 2007 Eastern Conference semifinal round.

#2. St. Louis Blues (47 seasons)

Not only have the Blues never won the Stanley Cup, they haven’t even been to the Finals since the first Nixon administration. To their credit, they were playoff regulars from the ’60s right through the early 2000s. But not since 2000-01 have they won more than one playoff series in a year, and have only even qualified about half the time.

#1 Toronto Maple Leafs (48 seasons)

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 either way, but it sure seems like Toronto fans are taking the Maple Leafs’ futility hard.

Not only have the Leafs not won it all since 1966-67, that’s also the last year they even made it to the Finals. Recent history has not been kind to the team, which just last season finally broke a seven-year run without a playoff appearance.

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