Fans of these ten clubs know about perennial misery all too well.

It’s time to stir up feelings of anguish and anger for fans of the remaining ten teams on this list. If you haven’t yet grabbed your drink(s), now would be a good time to start.

Part One of this list looked at positively perfect franchises, with all ten teams (and Vegas) having won at least one Stanley Cup this century. Part Two mainly looked at clubs who had experience some playoff success, but failed to reach hockey’s highest podium.

On the final installment of this series, teams with an utter lack of playoff success, or success at all for that matter, are featured on this list. While some of these teams have enjoyed solid regular seasons, and maybe even the odd playoff win, it hasn’t been accomplished with any consistency. What is consistent with these teams is that losing became commonplace for long stretches.

So, want to know who sucks the most this century? Read on to see who the ten most miserable franchises of the century are.

NHL’s 21st Century Misery Rankings: #31-#21

NHL’s 21st Century Misery Rankings: #20-#11

#10: Toronto Maple Leafs

Since 2000: 84 GP, 41-43 with a .488 winning percentage. Series Wins: 5 (T-21st). Made playoffs 8 out of 18 seasons.

Despite missing the Playoffs for ten of 11 seasons post-lockout, somehow the Toronto Maple Leafs aren’t as sad as other teams on this list.

That’s mainly because the Mats Sundin era in Toronto was filled with some good times. It brought about an intriguing Battle of Ontario rivalry in the early 2000’s, with superstar Swedes Sundin and Daniel Alfredsson battling head to head. It was a rivalry that Toronto dominated, as they knocked Ottawa out of the playoffs in four out of five seasons to start the century.

It’s hard to remember now, but the Leafs won seven series and made the Conference Finals twice dating back to the 1998-99 season. Then, everything cratered in the Six.

The Leafs had two seasons where they narrowly missed out on the postseason after the lockout, followed by five seasons where they were a terrible, boring team to watch. They finally made it back to the postseason during the lockout-shortened 2012-13 campaign, before they suffered one of the worst third-period collapses in playoff history.

Things are turning up in Leafland, and they will likely fall down the misery meter in due time. For now, the years of mediocrity still overshadows the Leafs, until they start to win in the playoffs.

#9: Buffalo Sabres

Since 2000: 65 GP, 33-32 with a .507 winning percentage. Series Wins: 5 (T-21st). Made playoffs 6 out of 18 seasons.

Similarly to Toronto, there was a time when Buffalo was a perennial playoff contender. There was even a two-year window where they were considered Stanley Cup favourites. That’s where most of the Sabres playoff success came from, when they made it to two Conference Finals between 2006 and 2007.

Sabres fans are probably still kicking themselves for the losses to both Carolina and Ottawa. Both of those series were winnable for Buffalo, but instead they remain Cupless throughout their 48-year history.

Their most recent success seems like forever-ago in Buffalo, now that the Sabres haven’t made the playoffs for seven straight seasons. They tried the tanking thing, only to fall short in drafting both Connor McDavid and Aaron Ekblad. Even though they’ve added some solid players since then, they were still the league’s worst team last season.

They now have Jack Eichel and Rasums Dahlin to lead a young-squad that has other impactful building blocks. Still, until this team starts to make the playoffs on a regular basis, they will remain one of the saddest teams in hockey.

#8: Calgary Flames

Since 2000: 67 GP, 30-37 with a .447 winning percentage. Series Wins: 4 (T-23rd). Made playoffs 6 out of 18 seasons. One Stanley Cup Final appearance (2004).

The Calgary Flames might not be the first franchise that comes to mind when you think of truly terrible teams this century. I mean, the face of their franchise, Jarome Iginla, is one of the best players of the last 20 years.

Unfortunately for the Flames in the early 2000’s, they had Iginla and not much else. They lacked good defence, goaltending, and secondary scoring. However, they started to put the pieces together, and were catapulted to the next level with the addition of Miikka Kiprusoff in 2003-04. That year, they came within one game of the Stanley Cup. One of the saddest components of that Flames run, was that things could have been different if it wasn’t for a controversial disallowed goal in Game Six.

I know Flames fans are still bitter about that but sorry, it wasn’t a goal.

That haunting memory does hold strong. Since then, the Flames have only won a single playoff series, in 2015 versus the Vancouver Canucks. They followed up their Stanley Cup appearance with four straight quarterfinal losses, and have a 15-26 postseason record since the 2004 playoffs.

#7: Edmonton Oilers

Since 2000: 61 GP, 27-34 with a .447 winning percentage. Series Wins: 4 (T-23rd). Made playoffs 5 out of 18 seasons. One Stanley Cup Final appearance (2006).

It is really hard to feel bad for the Edmonton Oilers after they won four Cups during the 1980’s. So? Don’t feel bad for them. Instead, celebrate the fact that they’ve been downright miserable for most of the 21st century, if that’s your sort of thing.

Other than a fluky Cinderella run to the Stanley Cup Finals in 2006, this team has been nothing short of a disaster. They spent most of the early 2000’s as a tweener team before their Cup run. Then, they spent the next decade nailing the draft lottery, only to fail at every aspect of putting a reasonable team together on the ice.

The result? Well, the Oilers were terrible for a ten-year stretch before finally reaching the postseason again in 2017. Even with Connor McJesus on their team, they still find new and creative ways to suck.

Let’s be real: McDavid has the talent to carry Edmonton into the playoffs year after year. Eventually though, they will need a supporting cast to get it done. There’s hope but hey, 30 other teams (maybe 29, sorry Ottawa) can say they have some semblance of hope moving forward.

#6: Minnesota Wild

Since 2000: 73 GP, 26-47 with a .356 winning percentage. Series Wins: 4 (T-23rd). Made playoffs 10 out of 17 seasons.

The Minnesota Wild are a bit of an outlier on this list. They are the only team in the bottom ten to make the playoffs more than they missed them in the 21st century.

Unfortunately for the Wild, they are the unofficial kings of making the playoffs, only to bow out immediately. Year after year, Minnesota has been considered a strong squad, but they always fail to impress when the games matter most. They had one Cinderella run to the Conference Finals in 2003 when they knocked off the powerhouse Avalanche in the Quarterfinals. Minnesota followed that up by knocking off the Canucks during the West Coast Express’s heyday, coming back from a 3-1 series deficit to do so.

Since then, it’s been a string of playoff failures for hockey-crazy Minnesota. They’ve only gotten past the first round twice in nine playoff appearances since their 2003 run. Both of the times they made it past Round Two, they were knocked out by the Blackhawks.

You do have to feel for this hockey mad fan base, even if they did enjoy a Cinderella run from the North Stars back in 1991. Despite all the regular season success, they haven’t come close to sniffing Lord Stanley.

#5: New York Islanders

Since 2000: 46 GP, 16-30 with a .347 winning percentage. Series Wins: 1 (29th). Made playoffs 7 out of 18 seasons.

See that first paragraph I wrote about the Edmonton Oilers? Yeah, you can insert that right here as well.

You can’t feel too bad for the Islanders after their run of four straight Cups in the 80’s. That doesn’t cover up the fact that the Islanders have been one of hockey’s most pathetic franchises in the 21st century.

Blame whoever you want, whether than be Garth Snow, meddling owner Charles Wang, Rick DiPietro, or John Tavares skipping town. For a plethora of reasons, the Islanders have been an irrelevant team since, well, the early 1990’s. They won their first playoff series in 2016 against the Florida Panthers, the first time they won a series since 1993. It looked like a sign of better times to come, but two years later the Islanders are further away from the Cup than ever before. They do have a good prospect pool, if that’s any solace for 25 years of losing.

#4: Arizona Coyotes

Since 2000: 37 GP, 14-23 with a .378 winning percentage. Series Wins: 2 (T-27th). Made playoffs 4 out of 18 seasons.

Things are about to get real sad, starting with the Arizona Coyotes.

Whether it’s constant relocation, ownership changes, or the fact that they haven’t made the playoffs in six seasons, the Coyotes continue to punish their remaining fans with mediocrity. They’ve only won two playoff series in 21 seasons since relocating from Winnipeg, and those both happened during the 2012 Stanley Cup playoffs.

2012 was actually the Coyotes third straight year in the playoffs, but before that the franchise had a run of another six seasons without playoff hockey. Like many teams who spend a good chunk of time near the bottom of the standings, the Coyotes do have a strong prospect pool. However, they do lack that elite game-breaking talent, although that hasn’t necessarily helped teams like the Oilers and Sabres anyways.

#3: Winnipeg Jets

Since 2000: 24 GP, 9-15 with a .375 winning percentage. Series Wins: 2 (T-27th). Made playoffs 3 out of 18 seasons.

If it wasn’t for the Winnipeg Jets run to the Conference Finals this season, I would confidently rank this franchise as the most miserable in hockey. Although the misery was broken up between fan bases, it’s certainly no surprise that no one cared about this team in Atlanta.

In 11 years, the Thrashers didn’t win a single playoff game. Then, the Winnipeg Jets went through another six seasons without winning a single playoff game.

For the record, that’s 17 years with eight playoff games and no wins. Yikes.

The Thrashers lucked into superstars Ilya Kovalchuk and Dany Heatley early on, but never did enough to build around them. You can blame Don Waddell, Rick Dudley, and the horrendous scouting staff who failed to build a successful team. Seriously, check out their draft history.

Through diligent drafting, the Jets look to finally have a contender. It’s been a loooooong time coming for this franchise. For the first time ever, the Jets/Thrashers incarnation can no longer be called pathetic.

#2: Columbus Blue Jackets

Since 2000: 21 GP, 5-16 with a .238 winning percentage. Series Wins: 0 (T-30th). Made playoffs 5 out of 17 seasons.

Neither fan base from that 2000 expansion has tasted any sort of glory or success throughout their 17 seasons of existence. While the Wild are the unofficial kings of bowing out of the playoffs early, the Blue Jackets are the actually the kings of losing in the playoffs. Not by quantity, but they do own the worst winning percentage in the postseason of all 31 teams since 2000.

It wasn’t even until the Blue Jackets eighth season of existence that they even made the playoffs. Even then, they got swept by the Red Wings before missing the playoffs for another four straight seasons.

Now, they’ve made the postseason in three of the past five years. They also look more competitive than they ever had before. Those are the good things. On the downside, if they lose Artemi Panarin (which sounds likely) then they’re back to lacking that game-breaking talent, unless Pierre-Luc Dubois, Zach Werenski or Seth Jones can find yet another gear. That, and Sergei Bobrosky hasn’t gotten it done in the playoffs. Things, for once, look bright in Columbus, but that could change in a hurry as well.

#1: Florida Panthers

Since 2000: 24 GP, 9-15 with a .294 winning percentage. Series Wins: 0 (T-30th). Made playoffs 3 out of 18 seasons.

Oh Florida, if only hockey was as easy as the 1996 playoffs.

Since that surprising run, the Panthers franchise has been an utter embarrassment to the NHL. They’ve made the playoffs in only four of the last 21 seasons, and have but six playoff wins to show for during that span.

They even went 13 seasons without a playoff win before finally getting three victories against the Devils during their first round defeat in 2012. In typical Panthers fashion, they followed that up with three more seasons out of the playoffs.

Imagine, packing it in for three years because you finally won a playoff game.

Things in Florida have been so bleak over the years, that even the local newspaper once wrote about how the Panthers should leave town. Yes, a Canadian team (cough, Quebec) would still support a losing team. I mean, four Canadian teams cracked the top ten on this list, and none of them have attendance issues.

Like other teams near the bottom of this list, the Panthers have young talent and are better positioned than they’ve been in a long time. Even so, they still only project as a fringe playoff team.

Just like the Arizona Coyotes and Atlanta Thrashers, it’s no surprise that most locals don’t care about the franchise. Their run of ineptitude is truly spectacular. For that, they rank as the most miserable franchise of the 21st century.