If there’s one thing all sports fanbases can relate to, it’s heartbreaking losses. Even the winningest sports teams have to go through pain before climbing the mountaintop.
But some fanbases certainly endure plenty more heartache and pain than others. For this list, we’re focusing on ten teams who have consistently performed well in the regular season, only to leave their fans devastated by the end of it all.
So, with that, let’s dive into ten sports teams who break their fans’ hearts every year.
Which sports teams constantly break the hearts of their fans each year?
Buffalo Bills
There are two special chapters of Buffalo Bills sports heartbreak. The first, of course, is the dynasty that never was: The Jim Kelly and Marv Levy-led group that reached four straight Super Bowls from 1990 to ‘93, only to lose every single one of them.
Even with other Hall of Famers in Thurman Thomas, Andre Reed, and Bruce Smith, the star-studded Bills could never get over the hump. Scott Norwood’s “wide right” miss in Super Bowl 25 began the jinx on Buffalo sports — and nothing has changed more than three decades later.
After nearly two decades of irrelevance, the Bills re-emerged as an AFC heavyweight with Josh Allen and Sean McDermot in 2019. The 2020 AFC Championship Game loss to the Kansas City Chiefs was supposed to be the start of a glorious run in Buffalo…or so we thought.
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Buffalo lost to Kansas City in “the 13-second game” a year later. Then, they were crushed by the underdog Cincinnati Bengals in the 2022 AFC Divisional Round after opening the year as Super Bowl 57 favorites.
A year later, Tyler Bass and “Wide Right II” ended the Bills’ season against KC yet again in the Divisional Round.
Seasons change, but the Buffalo Bills don’t. Same ol’ song and dance.
Los Angeles Clippers
The Clippers could never breakthrough in the “Lob City” era with Blake Griffin, Chris Paul, and DeAndre Jordan. Despite six straight playoff appearances from 2012 to 2017, the Clippers won just three playoff series and never advanced past round two.
When the Clippers landed BOTH Kawhi Leonard and Paul George in the summer of 2019, it was supposed to mark the beginning of the golden era for the Los Angeles Lakers’ little brothers, if you will.
But here we are a half-decade later, and it’s just the same old Clippers. They dominate the regular season, then fold like a soft pretzel in the postseason.
Since landing both Leonard and George, the Clippers have won a whopping three postseason series — two of which came in 2021 alone.
They reached the Western Conference finals for the first time in franchise history that year, but Leonard’s season-ending injury in round two was another painful reminder that the Clippers couldn’t have nice things. They wound up losing to the Phoenix Suns in six games.
LA has failed to win a single playoff series since their run to the 2021 conference finals, even with two shoo-in Hall of Famers leading the way. Heck, landing former MVP James Harden during the 2023-24 season did nothing but lead to another round-one exit.
Wanna know why? Because Clippers fans have to endure miserable heartbreak every year.
Dallas Cowboys
Some fanbases may be irked by this entry, asking us how we could feature a sports team with five Super Bowl championships to their names. Well folks, let us tell you something.
There are two generations of Cowboys fans who can only sample a Super Bowl by watching highlights of the glory days from the ‘70s and ‘90s. Cowboys fans born in the new millennium, along with the millions of old-timer supporters, never get to celebrate anything.
Dallas hasn’t played in an NFC title game since 1995 — the last year they won the Super Bowl. Since winning Lombardi Trophy No. 5, Jerry Jones’ squad has had four playoff wins — all wild card round victories.
This team never broke through with Tony Romo, Terrell Owens, DeMarcus Ware, Dez Bryant, Zack Martin, Tyron Smith, Ezekiel Elliott, et al.
Though Dak Prescott puts up MVP-like numbers every year, the guy only has two playoff wins to his name. Dallas churns out a top-10 offense AND defense each year, yet it always culminates with a wild card or divisional-round loss.
‘Least the ‘90s were fun…
Cleveland Guardians
Unfortunately for Cleveland fans, there was only room for one champion in the 2016 World Series. That wound up being the Chicago Cubs, who won Game 7 in “The Land” to end the franchise’s 108-year World Series drought.
With the Cubs emerging victorious, the longest World Series drought changed ownership and fell into the hands of Cleveland. And since losing the 2017 Fall Classic on their home field, the Guardians have only added more layers of crushing losses for their fans to stomach.
After winning 102 games in 2017, the Guardians were ousted by the underdog New York Yankees in five games. They were swept by the Houston Astros in the 2018 ALDS.
Two years later, their return to the postseason ended with a sweep at the hands of the Yankees. Then, after taking a 2-1 series lead over the Pinstripes in the 2022 ALDS, the Guardians lost two in a row and saw another division-winning season go to waste.
Factor in Cleveland blowing a 9th-inning lead in Game 7 of the 1997 World Series against the Florida Marlins…and blowing a 3-1 series lead against Boston in the 2007 ALCS…and it’s hard not to feel for Guardians fans.
Phoenix Suns
The Suns couldn’t break through with a championship in the Charles Barkley era, losing to Michael Jordan and the dynastic Chicago Bulls in the 1993 NBA Finals.
The Suns re-emerged as a contender in the mid-2000s, thanks to Steve Nash’s arrival in 2004. Nash won consecutive MVPs in 2005 and ‘06, working alongside Shawn Marion and Amar’e Stoudemire to form a dynamic “big three” in The Desert.
But Phoenix could never get past the Dallas Mavericks, San Antonio Spurs, or Los Angeles Lakers’ roadblocks — losing in the 2005, ‘06, and 2010 Conference Finals. The Spurs and Lakers formed 21st-century dynasties, and the Mavs finally broke through with their first title in 2011.
The Chris Paul-Devin Booker tandem brought relevance back to Phoenix in 2021 as the Suns made a thrilling run to the NBA Finals. But it was all for nothing again. They took a 2-0 series lead over Giannis Antetounmkpo’s Milwaukee Bucks in the NBA Finals, only to lose four in a row.
The Suns looked poised to rebound from the heartbreak, winning 64 games the following season. But that only ended with another gut-wrenching loss, as they were ousted by the Dallas Mavericks in Game 7 of the conference semis.
Phoenix traded for Kevin Durant ahead of the 2023 deadline, hoping the future Hall of Famer would get them over the title hump. NOPE. Just another loss in the conference semis, this time to the eventual champion Denver Nuggets.
So then in the 2023 offseason, the Suns acquire superstar guard Bradley Beal to complement KD and Booker. All that led to was a first round sweep at the hands of the Minnesota Timberwolves.
The Arizona Cardinals and Arizona Diamondbacks have been mostly irrelevant this century. The Arizona Coyotes just moved to Utah. Copper State sports fans rely heavily on the Suns, but all they do is burn away this city’s hopes of another championship each year.
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Boston Bruins
It’s odd to put the Bruins on this list since their last Stanley Cup victory wasn’t all that long ago. 2011, to be exact.
Throw in how much Boston has been spoiled with team sports success in the 21st century, and it’s truly difficult to shed a tear for supporters of the “Original Six” franchise.
But from 2012 to the present, the Bruins have suffered an unbelievable amount of devastating defeats that sometimes make you forget this team broke through in 2011.
They watched the Chicago Blackhawks and St. Louis Blues skate around with the Stanley Cup on their home ice in 2013 and 2019, respectively. Against St. Louis, Boston put up a stinker in a gut-wrenching 4-1 home defeat that saw the Blues win their first Stanley Cup.
Boston also suffered season-ending Game 7 losses at home against the Washington Capitals in 2012, the Montreal Canadiens in 2014, and the Florida Panthers in 2023. Against Florida, Boston blew a 3-1 series lead and lost in OT after setting the regular-season records for wins and points.
The Bruins have only missed the playoffs twice since 2008. Three Presidents’ Trophies. Three Conference Finals. Superstar power featuring David Pastrnak, Brad Marchand, Patrice Bergeron, Charlie McAvoy, Tuukka Rask, Jeremy Swayman…you name it.
And no Stanley Cups to show for it since 2012? I mean, even the New England Patriots and Boston Red Sox went on to achieve dynastic status after winning it all in 2001 and 2004, respectively.
New York Yankees
If not the Cowboys, the Yankees are the most hated team in North American professional sports leagues. So please shed a tear for those poor Yankees supporters who haven’t been able to celebrate a World Series championship since 2009.
The Yankees are awfully similar to the Boston Bruins. Their last world championship was a little over a decade ago. They’re a title contender every year. But once the calendar flips to playoff time, the Yankees and Bruins both crumble like cookies.
Since 2010, the Yankees have lost in the ALCS FIVE times. And let’s not forget their decisive Game 5 loss to the Tampa Bay Rays in the ALDS. Or their crushing playoff losses to the bitter rival Red Sox in the 2018 ALDS and the 2021 AL Wild Card Game.
The Yankees are loaded with star power, namely Aaron Judge, Gerrit Cole, Giancarlo Stanton, Clay Holmes, and DJ LeMahieu. They always boast a deep farm system and one of baseball’s highest payrolls, yet they can’t even buy an AL pennant out of it?
Nobody feels sorry for the Yankees except their very own fanbase. I mean, it’s pretty unbelievable how many great regular-season campaigns and superstars’ prime years have gone to waste with constant October choke jobs.
Philadelphia 76ers
Since 2018, only the Milwaukee Bucks, Boston Celtics, and Denver Nuggets have won more games than the 76ers. The difference is that those three sports teams are in the title mix every year, while the 76ers are nothing more than regular-season darlings.
Even with all-world superstar Joel Embiid and terrific sidekicks like Jimmy Butler, Ben Simmons, Tobias Harrison, James Harden, and Tyrese Maxey, these 76ers have never managed to break through in a wide-open Eastern Conference.
Their most painful loss was unquestionably Kawhi Leonard’s game-winning buzzer-beater in Game 7 of the conference semis series against the Toronto Raptors. Two years later, the top-seeded 76ers were ousted by the fifth-seeded Atlanta Hawks in seven games.
Philly held a 3-2 series lead over the archrival Celtics in the 2023 Conference Semifinals…only to lose the next two games. A year later, the 76ers were eliminated by the New York Knicks in the opening round.
The 76ers are basically the Eastern Conference version of the Clippers. They are never short on star power and future Hall of Famers, but they always choke and leave their fans wondering what could have been. Every. Single year.
Toronto Maple Leafs
Not much more can be said about the Maple Leafs and the cruel heartbreak they cause their fans annually.
They have the longest active Stanley Cup drought, having last won it all in 1967. In fact, that’s the last year Toronto actually reached the championship series. The Chicago Blackhawks had the longest cup drought from 1961 to 2009 before finally ending it in 2010.
In the post-lockout era—2005-06 onward—the Leafs have won a single playoff series. The annual playoff chokejobs include four Game 7 losses to the rival Boston Bruins, two of which came in overtime.
A core with superstars Auston Matthews, Mitch Marner, William Nylander, and John Tavares just keeps falling short time and time again.
They blew a 3-1 series lead to the underdog Montreal Canadiens in the opening round in 2021. They blew three separate series leads in their opening-round loss to the Tampa Bay Lightning in 2022, suffering another brutal Game 7 loss on home ice.
The Maple Leafs seemingly finally broke through in 2023 by eliminating Tampa Bay to win their first playoff series since 2004…only to be dispatched by the eighth-seeded Florida Panthers in five games.
And in the opening round of the 2024 postseason? Just another Game 7 overtime loss to the Bruins…
The Maple Leafs, dare we say, are the NHL’s version of the Dallas Cowboys. It’s all hype and no results every year.
Minnesota Vikings
This one doesn’t need a lot of explanation now, does it?
Legendary head coach Bud Grant led Minnesota to four Super Bowl appearances between 1969 and ‘76. The Vikings lost all four of them by double digits.
Then you had Gary Anderson’s miss in the 1998 NFC title game that wasted the Vikings’ 15-win, record-setting season. What about Brett Favre’s brutal interception in the 2009 NFC title game when Minnesota was on the verge of defeating the New Orleans Saints?
Blair Walsh’s missed gimme vs. the Seattle Seahawks in the 2015 wild card round? Getting blown out by the Eagles in the 2017 NFC title game when you were ONE VICTORY away from playing Super Bowl 52 inside your own stadium?
The Vikings are never terrible. They’re in playoff contention every year. Yet all they do is add more and more “how did that happen” losses to their repertoire, constantly blowing grade-A chances of winning the franchise’s first Super Bowl.
Sports are a cruel thing, and Vikings fans can tell you that better than anyone.
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