What was Your Saddest Sports Season Ever?

By Matt McEwan in News
Published:

Each year one of 32 NFL teams hoists the Vince Lombardi Trophy as Super Bowl champions, one of 30 NBA teams claims the Larry O’Brien Trophy as NBA Champions, one of 30 MLB teams wins the World Series, and one of 31 NHL teams raises the Stanley Cup.
But while these four fan bases are enjoying the euphoric feeling of supporting a champion, there is upwards of 119 other groups of diehard fans left with a whole in their heart, saddened as they have to enter the offseason with nothing other than, “there’s always next year”.
Personally, this has to be the saddest sports season of all-time for me.
Not only did the #Leafs make me re-live the horrors of 2013, but the #Raptors truly put forth one of the most embarrassing efforts from a 1-seed I’ve ever seen. To tie a bow on it, my #Broncos had one of their worst seasons ever … #saddestsportsseason pic.twitter.com/TeqIrWn8Ij
— Matt McEwan (@Matt_McEwan) May 10, 2018
We asked you guys to share in the sadness, and you certainly came through for us, proving that misery in fact does love company. Here were some of the best replies we received on Twitter:
Your Saddest Sports Seasons
Gotta give it up to Chris here. Not only is he strong enough to talk about those three devastating events, but he still supports his teams after they stomped all over his heart.
When Trey Burke hit the deep three to force OT agaisnt KU, When Zach Randolph got suspended for game 7 vs OKC and when the Chiefs lost to the Titans in the playoffs. All three were heartbreak #saddestsportsseason pic.twitter.com/kIlmLqFysP
— Chris Kern (@chriskern11) May 9, 2018
“The worst officiating in league history” may be a tough claim to pass. But we won’t call Warren on it here. Those are the words of a passionate fan who just had his heart ripped out of his chest and stomped on.
When the 2002 Lakers beat the Kings on this shot and eventually win the series behind the worst officiating in league history….#saddestsportsseason pic.twitter.com/TS1rNyOGpQ
— Warren Shaw ?? (@ShawSportsNBA) May 10, 2018
I can remember the champions league final of 2008, Chelsea v Man Utd. Poor ol John Terry had a bit of a slip taking what would have been the winning penalty. He missed, Utd went on to win!!! Argh!! #saddestsportsseason pic.twitter.com/jztEPBAUGf
— Gary Alder (@gartommat) May 9, 2018
It’s one thing to sit through your favourite team’s worst season ever. But it’s a whole other kind of hurt when it also costs you money.
In 2014, Vegas set the win total for the Knicks at 41.5. I remember talking to my friend and we couldn’t get over how much of a lock taking the over was. So we did. Fast forward 7 months and the Knicks won 17 games in total. Worst bet ever. #saddestsportsseason
— Justin Birnbaum (@JustBirny) May 14, 2018
Gotta feel for Justin here. The guy has suffered through more heartbreak than he can describe in 280 characters.
In 2007/2008, the Mets collapsed to miss the postseason. In 2007, they were seven games up 17 to go. In 2008, they were in control of the Wild Card, but faltered tragically in September. Just two of the painful symptoms of the Mets from 2006-2015. #saddestsportsseason
— Justin Birnbaum (@JustBirny) May 14, 2018
#tsv1860 will play the promotion playoffs against Saarbrücken. The club was double relegated from the second division to the fourth division and had all its youth teams relegated. After winning their division this year they are not guaranteed promotion. #saddestsportsseason
— Manuel Veth (@ManuelVeth) May 10, 2018
This may be Ryan’s saddest season for now, but that’ll change when he has to pay up on our NBA Finals bet this year …
San Antonio’s 2012-13 season. Ray Allen’s game-tying three still haunts me in my dreams. #saddestsportsseason pic.twitter.com/hTJDCktA4r
— Ryan Murphy (@ryanjamesmurphy) May 9, 2018
Shoutout to the guy who put a smile on our faces as we were pouring our hearts out. “WIIIIIILLLLLSSOOOOOOOONNNNNN”
When Wilson resigned from the Vendee Globe yacht race. pic.twitter.com/EeKnCBm9MJ
— Shep (@jjayshep) May 9, 2018
No way this guy cheers for the Browns then …
Georgia Tech’s 1-10 1994 Season. Just a handful of years after a national title and then the bottom fell out. I never felt so low as a football fan.
— Jeff or Jeffrey Fann (@TalkinACCSports) May 9, 2018
Kawhi Leonard may not be done breaking hearts, but at least he can’t hurt San Diego sports anymore.
SDSU had a serious chance to win the 2011 National Championship. Our team went 34-3 best team in school history. Kawhi Leonard balling out. Losing a close Sweet 16 Game (67–74) to UConn due to ridiculous calls and a few flops. UConn wins the 11 Championship. #ShouldHaveBeenUS.
— San Diego Sports (@SanDiego_Sports) May 10, 2018
Joe, are you saying you didn’t feel better when the league came out and admitted that would have been a TD under the “new catch rule” …?
Jesse James’ touchdown not a touchdown BS replay review fiasco from Week 15 this past NFL season is probably the most disgusted (and cheated) that I’ve felt about ANY sports event in my entire life!
— Joe Kuzma (SCU) (@joe_kuzma) May 9, 2018
Yeah, it’s been a rough go lately as a Knicks fan.
This season. Porzingis ACL, Ntilikina looked like he regressed throughout the season, Noah for two more years, capped out for two years, and won just enough to probably get a crappy draft pick. So no hope on the horizon and Dolan still owns the team.
— NYKnicksPodcast (@NYKnicksPodcast) May 11, 2018
You had to know this was coming:
Every Browns season
— Fynx (@fynxgaming) May 9, 2018
Watching this game was painful for more than just Rams fans. It just seemed like the Patriots knew every play that was coming …
Losing a franchise aside, as a St. Louis fan, that loss to the Patriots in 2001 as a two touchdown favorite was particularly painful. The potential butterfly effects of the Patriots losing that Superbowl are crazy to think about.
— Braxton Angle (@Braxton_Angle13) May 10, 2018
Is this a bad time to remind you I’m a Broncos fan?
There have been many Super Bowls, but only one GOLDEN Lombardi. My team should have won, more talented, and with a dominant season. Mike Shula struck again, and we lost.
— 7poundbagdotcom (@7poundbagdotcom) May 10, 2018
Hey, what does Forbes know?
Being a Detroit Lions fan is rough. Not only did @Forbes estimate us to be the 31st team in overall value. We were also the first team to go 0-16. Not to mention every game seems to end in a 4th quarter meltdown…
— Endzoneblog.com (@EndzoneblogNFL) May 9, 2018
But at least you have a franchise quarterb … oh, boy
I am a Phoenix Suns fan so every season is pretty sad. Also my Colts are doing too well either. Both seem to have ownership issues so it probably will not change
— Shawna Hudson (@Hudsonwife16) May 9, 2018
You know it was pretty dramatic when they make a movie out of it:
2004 ALCS #woof
— Ben Chapman (@ChapmanBA) May 9, 2018
At least the Canucks’ Stanley Cup window wasn’t closing …
2011 game 7 NHL playoffs. Canuck get blown out by Marchard and the Bruins. And my city goes up in flames?
— Spencer L (@Spencerjlindsay) May 8, 2018
At least Shep’s off-topic tweet was funny. This Sascha guy stepped outside of our favorite sports teams to still bring a tear to our eye.
No question, Season 5 of Friday Night Lights. #saddestsportsseason
— Sascha Paruk (@SaschaParuk) May 8, 2018
Keep your eyes on our Twitter for more “fun” opportunities to have your sports opinions heard!

Editor-in-Chief; Sports Betting Expert
With nearly a decade working in the industry, Matt is a seasoned sports betting veteran. He got his start with SBD in 2016 and worked his way up the ladder to become the Editor-in-Chief. Along the way he has done everything from reviewing sportsbooks to creating proprietary sports betting tools.