Despite some playoff success, the 21st century has delivered overwhelming misery to many of these franchises.

Even though this is only the second installment in the series, it might be time to bust out the tissues.

While part one of this series looked at Stanley Cup Champions (and Vegas), part two focuses on teams who have enjoyed some playoff success, but mostly misery, over the last 18 seasons.

I explained my rationale in part one of these rankings, since they get more convoluted after the Stanley Cup winners of the 21st century. Generally, I ranked teams with some playoff success ahead of completely inept franchises. As a fan, wouldn’t you rather see your team compete and fail rather than just fail for years on end?

There is only one Stanley Cup Champion on this list who didn’t make it into part one of this series, and they can take, ahem, pride in being the saddest Cup champion of the century. What a title!

Without further ado, here are teams #20 through #11 on the NHL’s 21st Century Misery Rankings.

• NHL’s 21st Century Misery Rankings, #31-#21

#20: Dallas Stars

Since 2000: 99 GP, 48-51 with a .484 winning percentage. Series Wins: 8 (T-16th). Made playoffs 9 out of 18 seasons. One Stanley Cup Appearance (2000).

The Dallas Stars have less playoff appearances than most teams on this list, and they’ve missed the playoffs in eight of the last ten seasons. So why does Dallas come in at only 20th overall on the misery meter?

In my guidelines, I did say that recency bias would play into the rankings. Although Dallas hasn’t won a Cup this century, they were the last winners of the 20th century. The Stars beat out the Buffalo Sabres for hockey’s biggest prize thanks to Mike Modano, Brett Hull, Sergei Zubov and Ed Belfour. That core led the team to three more division titles at the turn of the century, along with another appearance in 2000 Stanley Cup Finals.

Even though they missed the playoffs for five straight years from 2009 to 2013, the Stars were never bad enough to bottom out and draft high. They obtained their best players either through trade or through the fifth round of the draft (Jamie Benn, 2007, John Klingberg, 2010). 2015-16 looked like a turning point for the franchise, but they’ve suffered through two more disappointing seasons since. Hey, at least their last Cup win was during the last 20 years.

#19: Carolina Hurricanes

Since 2000: 72 GP, 39-33 with a .541 winning percentage. Series Wins: 9 (15th). Made playoffs 4 out of 18 seasons. Two Stanley Cup Final appearances (2002, 2006), One Stanley Cup win (2006).

Without a doubt, the Carolina Hurricanes are one of the most bizarre teams of the 21st century. Should their fans be sad, hopeful, or thoroughly confused?

In terms of recency, fans are assuredly fed up after nine years without postseason hockey. However, the Canes have enjoyed playoff success, and actually have one of the best winning percentages in the postseason over the last 18 seasons.

Carolina has only made the playoffs five times in 20 seasons of existence, and four times this century. Of those four playoff appearances, they have one Quarterfinals loss in 2000, one Conference Finals loss in 2009, one Stanley Cup Finals loss in 2002, and of course, they won it all in 2006.

The problem is, they’ve missed the postseason more than all but two teams over the last 18 seasons. Despite making the playoffs so sporadically, they’re still 15th overall in playoff victories in the last 18 years. Unlike those downtrodden franchises, the Hurricanes can still holds their heads high with a lone Stanley Cup victory. Congratulations to the saddest Stanley Cup winners of this century!

#18: New York Rangers

Since 2000: 129 GP, 61-68 with a .472 winning percentage. Series Wins: 11 (T-9th). Made playoffs 11 out of 18 seasons. One Stanley Cup Final appearance (2014).

For a team that had an ownership group with deep pockets, the Rangers were never patient enough to build through the draft. That’s resulted in a bunch of playoff games, but not much actual success.

After winning the Cup in 1994 (ripping out the hearts of Canucks fans everywhere), the Rangers enjoyed three more seasons of success before a run of seven straight playoff misses before the 2004-05 lockout.

2005-06 was the start of the Henrik Lundqvist era in New York, where the team made the playoffs for 11 of 12 seasons before announcing their rebuilding plans in 2018. There was a smattering of different results, but the closest they came to recapturing their Cup glory was in 2014, when the Rangers bowed out rather easily against the Los Angeles Kings.

#17: Philadelphia Flyers

Since 2000: 149 GP, 74-75 with a .496 winning percentage. Series Wins: 12 (8th). Made playoffs 14 out of 18 seasons. One Stanley Cup Final appearance (2010).

Philadelphia Flyers fans might cry out that they’ve been hard done by over the years, since they haven’t won a Stanley Cup since 1974-75. They have enjoyed a fair amount of playoff success considering, even if they’ve only made the dance once this century.

From the early 2000’s squads with Eric Lindros and John Leclair, to the Mike Richards and Jeff Carter backbone, all the way up to the Claude Giroux and Jakub Vorachek led-Flyers, this team has remained competitive. The playoff success hasn’t necessarily been there, and they can largely thank their state rivals, the Pittsburgh Penguins for those woes.

However, their Cup Final appearance in 2010 was largely a Cinderella run. Chris Pronger anchored the defence, and heroes such as Daniel Briere were outstanding. However, they certainly didn’t have a deep defence or a formidable goaltending tandem. By all accounts, they should have been knocked out in the Semifinals, if it wasn’t for an epic collapse from the Bruins.

It’s been a while since Philly has won a Cup, but their fans have had plenty of playoff hockey to enjoy this century. They’ve also been playoff competitors, rather than Stanley Cup favourites.

#16: Ottawa Senators

Since 2000: 129 GP, 64-65 with a .496 winning percentage. Series Wins: 10 (T-13th). Made playoffs 13 out of 18 seasons. One Stanley Cup Final appearance (2007).

Over the next couple of seasons, it’s quite possible that the Ottawa Senators will become the most miserable team in hockey. Things look bleak in the nations capital with scandals galore, their best player leaving town, and the looming possibility of losing the first overall pick next season.

However, the Senators have been a plucky and surprisingly successful franchise. They haven’t gone through a dreadful stretch, although it looks like their time is about to come. Ottawa went on a run of 11 straight seasons in the playoffs from 1996-97 to 2008-09. Their Cup run in 2006-07 was their best chance to win the Cup, but they ran into a far superior Anaheim Ducks team.

The Senators went on an improbable run in 2016-17, but fell to the Pittsburgh Penguins in Game Seven overtime of the Eastern Conference Finals. Similarly to the Flyers, the Senators have always been playoff competitors rather than Stanley Cup favourites. They’ve fallen victim to a superior Penguins team many times over the last decade, with Pittsburgh eliminating them from the playoffs in four of their last six appearances.

#15: Nashville Predators

Since 2000: 105 GP, 49-56 with a .466 winning percentage. Series Wins: 7 (T-18th). Made playoffs 11 out of 18 seasons. One Stanley Cup Final appearance (2017).

Unlike some teams on this list, Nashville is starting to turn their woes around. Their existence began with five straight playoff misses, before they became a fringe playoff team that always lost in the first round. Nashville finally got past the first round on their sixth attempt, and it wasn’t until 2017 that they finally got past the second round, reaching the Stanley Cup Final against the Pittsburgh Penguins.

Nashville wasn’t given an easy ride entering the league. Expansion rules weren’t friendly to them, and general manager David Poile has slowly built up a perennial contender after years of schrewd moves.

You have to give Nashville fans credit. They have one of the league’s craziest followings, even though their team hadn’t found success until recently. With Nashville now icing a deep team that can compete for the Stanley Cup, expect them to move slowly down the misery rankings.

#14: Montreal Canadiens

Since 2000: 111 GP, 48-63 with a .432 winning percentage. Series Wins: 8 (T-16th). Made playoffs 11 out of 18 seasons.

The Montreal Canadiens might be the most storied franchise in the history of the NHL, but the 21st century has been a different story for the organization.

If there’s anyone who defines “tweener team” this century, it’s the Canadiens. They haven’t missed the playoffs for more than one year consecutively since the turn of the century, when they missed for three seasons. That’s likely to change in the coming season, but for the most part the Canadiens have always challenged for a playoff spot.

What’s eluded them this century, however, is elite talent. They have one of the best goaltenders in the world in Carey Price, but players like Saku Koivu, an older Alex Kovalev, Max Pacioretty and a banged up Shea Weber aren’t the elite players the organization craved. Because of that, they’re only one of ten franchises not to play for the Stanley Cup this century. They have two Conference Final berths, but lost to the Flyers in 2010 and the Rangers in 2014.

Even though it’s been a tough century for the Canadiens, it is hard to feel too bad for the most storied franchise in NHL history. It’s not like they’ve been a laughingstock, but playoff success has escaped them.

#13: St. Louis Blues

Since 2000: 110 GP, 47-63 with a .427 winning percentage. Series Wins: 7 (T-18th). Made playoffs 12 out of 18 seasons.

The next three teams here are arguably three of the most notable playoff chokers on this list (I might have saved one more for the top ten). In case the surprise isn’t ruined for you already, the top ten most miserable teams are largely made up of teams who don’t even know what the playoffs are.

St. Louis knows the playoffs, but they don’t know much about winning in the postseason. For most of this century, St. Louis has been a model franchise in the regular season. They’ve rostered some good teams, largely on the back of solid defence and depth up front. However, they’ve still yet to even reach the Stanley Cup Finals since they were an expansion squad in the late 1960’s.

The Blues did go through a rough stretch where they missed the playoffs in five of six seasons between 2006 and 2011. In their only playoff appearance, they were swept by the Vancouver Canucks.

Once again in 2018-19 St. Louis has retooled and added some pieces that might be able to get them a few extra playoff wins, but they’re up against it to make their first Stanley Cup Final berth in nearly 50 years. You do have to give St. Louis’ management credit though for drafting well, making schrewd moves, and staying competitive. They just need to take that next step towards glory.

#12: Vancouver Canucks

Since 2000: 105 GP, 47-58 with a .432 winning percentage. Series Wins: 7 (T-18th). Made playoffs 11 out of 18 seasons. One Stanley Cup Final appearance (2011).

I know many of you might have expected to see the Canucks lower on this list. Hey, Canucks fans are prominent here and we’ve all been through pain watching this team.

Still, entering the 2000s, this team was a playoff contender on the backs of the West Coast Express line. After the lockout, the Sedins largely led this team into the playoffs year after year. The Canucks have missed the playoffs in four of the last five seasons, but before that they were always in the postseason conversation. They missed the playoffs during the 1999-00 season (their fourth straight miss), before making the playoffs in 10 of 12 seasons.

Although the Canucks have made it to the Finals ahead of teams like St. Louis and Montreal, they’ve always found new creative ways to lose and break the hearts of fans in this city. There were the multiple defeats to Chicago, a crushing loss against the eighth-place Kings in 2012, the Dan Cloutier gaffe, the loss to Minnesota following Todd Bertuzzi’s guarantee, and the infamous Game Seven against Boston.

Damn, how many bad memories can I stir up in one sentence?

Now, the Canucks are slowly creeping up the misery meter with a team destined for a fourth straight playoff miss in 2018-19. The ineptitude of the current management group, coupled with a plethora of bad playoff losses leaves the Canucks as one of the most miserable playoff contenders this century.

#11: San Jose Sharks

Since 2000: 184 GP, 94-90 with a .510 winning percentage. Series Wins: 16 (T-3rd). Made playoffs 16 out of 18 seasons. One Stanley Cup Final appearance (2016).

Part two of this list is littered with teams who’ve had decent playoff success, but haven’t won a Cup. However, the San Jose Sharks have utterly let their fans down with a lack of a Cup, considering how good they’ve been this century.

Think about this: the Sharks have made the playoffs in 16 of the last 18 seasons. They have the third-most playoff victories this century behind Detroit and Pittsburgh (who, by the way, have a combined five Cups this decade). Somehow, they find new and creative ways to lose each year.

Even with all those playoff games, this team has only made the Stanley Cup Finals once. It’s almost unfathomable to think that a team can make the playoffs with this much regularity, only to bow out so often.

Of their 16 playoff appearances, the Sharks have gotten past the first round 11 times, but have only gotten past Round Two four times. The second round has been their kryptonite, and 2017-18 was no different. They were favoured against the expansion Golden Knights, but once again they were outclassed.

Despite loads of talent on their roster, the Sharks have never been able to get it done. Hey, at least their fans have enjoyed tons of playoff hockey over the years. Only Pittsburgh has played more games in the postseason since 2000. Unlike Sharks fans however, Pens fans have had plenty of time to celebrate over the years.