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What was Your Saddest Sports Season Ever?

A young Yankee fan shedding tears.
No matter how many championships your team has won, you'll never forget the heartbreak. Photo by slgckgc (flickr) [CC License].

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.


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.


“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.




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.


Gotta feel for Justin here. The guy has suffered through more heartbreak than he can describe in 280 characters.



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 …


Shoutout to the guy who put a smile on our faces as we were pouring our hearts out. “WIIIIIILLLLLSSOOOOOOOONNNNNN”


No way this guy cheers for the Browns then …


Kawhi Leonard may not be done breaking hearts, but at least he can’t hurt San Diego sports anymore.


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” …?


Yeah, it’s been a rough go lately as a Knicks fan.


You had to know this was coming:


Watching this game was painful for more than just Rams fans. It just seemed like the Patriots knew every play that was coming …


Is this a bad time to remind you I’m a Broncos fan?


Hey, what does Forbes know?


But at least you have a franchise quarterb … oh, boy


You know it was pretty dramatic when they make a movie out of it:


At least the Canucks’ Stanley Cup window wasn’t closing …


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.

Keep your eyes on our Twitter for more “fun” opportunities to have your sports opinions heard!

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After receiving a bachelor's degree in communications, Matt spent two years with Rogers TV as a host, producer, and play-by-play commentator. He has been with us since 2016 and serves as SBD's editor-in-chief and sports betting expert.