What sports moment broke your heart the worst?

I was a HUGE Daryl Waltrip fan for decades however, when Dale Sr. won the Daytona 500 in 1998 after many years of coming close, every single person on every single team on Pit Road spontaneously lined up to high five the greatest sports car driver of our generation. At times, I hated Dale cuz he knew how to win and beat my man DW but, you have to respect his unabashed style of racing in the 70s, 80s and 90s. Dale Earnhardt was The Intimidator , and I simply cannot watch that replay without tearing up. Pat's diagnosis was a close second.
 

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"The Catch"
2001 SEC Championship game
4th and 26 Florida loss
Tottenham 2-0 Champions League finals loss to Liverpool Last year
 
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Gaffney catch
Colquitt blown wheel
2001 SEC title game
The entire Arian Foster fumble era
The "Hobb Nail Boot" Georgia loss
The Pig Howard fumble through the end zone (another Georgia loss)
The Dooley era
When Cutcliffe left for Ole Piss and Randy "Freaking" Sanders took over as OC
The Claw-fense
The day Fulmer was fired and our spiral into CFB irrelevancy began
 
he was one of the worst announcers I ever heard - couldn’t listen for two minutes to a game he was calling.
My big brother jinx was at the game with son. After we scored to go up with 26 seconds to go, my little chug nephew was happy and said, “We won!”. The jinx spoke up and said, “Not yet.”, and then we proceeded to lose.

For years I got blamed my jinxfulness due to the fact I called my daddy for an update right after we scored(I was at work and didn’t have a clue.) . It didn’t take long to hear the rest of the story. After that my dad was done giving updates. I told him over and over that the real jinxes were all his other sons. He would laugh and play along, but I have always known he thought I was a UT jinx too.
Get better Vols. You gotta a lot of jinxes to overcome. We aren’t going anywhere. Except for as many games as we possibly can.
 
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Hard to say. I do remember feeling bad for Ivan Lendl when he went out in the fourth round of Wimbledon in '92. He was my favorite non-American tennis player. Really wanted him to get the career Grand Slam. 2008 Masters was heartwrenching. Felt so bad for Snedeker.
 
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1976 VMI loss with Bernard King not playing. Bunch of 6-4 guards shot 66 percent or so with almost all shots beyond 15 feet. That was brutal, but 1977 loss to Syracuse was worse because we had national championship caliber team. I still haven't gotten over either of those losses.
The Orangemen's match-up 2-3 zone was too much for the Vols. Didn't UK with the Natty? Didn't we beat them twice?!
 
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I gotta go with these,those Falcon games are what made me not like the Cowboys.
I was at that 78 Falcon game,we were up going into the 4th quarter,Roger Staubach was injured and Danny White comes back and beat us.That was the year we had the best defense in the league,and still is the lowest average scoring record,like 12 points a game.Boy was it cold that day.
 
I was at that 78 Falcon game,we were up going into the 4th quarter,Roger Staubach was injured and Danny White comes back and beat us.That was the year we had the best defense in the league,and still is the lowest average scoring record,like 12 points a game.Boy was it cold that day.
I still remember the Falcon's middle linebacker knocking Staubach out of the game.
 
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I was at that 78 Falcon game,we were up going into the 4th quarter,Roger Staubach was injured and Danny White comes back and beat us.That was the year we had the best defense in the league,and still is the lowest average scoring record,like 12 points a game.Boy was it cold that day.
Yep,,it was the first time I had that sick helpless feeling of "I cant believe this". That defense was definitely the best I've seen the Falcons have.
 
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The Orangemen's match-up 2-3 zone was too much for the Vols. Didn't UK with the Natty? Didn't we beat them twice?!
Marquette Beat UNC in the finals. UNC Charlotte made the final four. We beat UNCC with Cornbread Maxwell earlier in the year. All that makes it more painful.
 
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2015 loss to Florida. I was listening to the very end on radio, which made it even more of a gut punch. When we kicked the field goal, Bernie said "Goooooo. No I'm sorry." Talk about going from joy to sorrow in under a second.
 
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2010 Michigan State. Losing by a point in the Elite Eight to a team we were better than will sting forever.
 
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Just about every throwback Kentucky basketball game that CBS has broadcast over the last few weeks.
 
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10 most painful losses in Tennessee history for me. In no particular order.
1) 2001 SEC Championship vs LSU
2) 1990 vs Bama
3) 2000 vs Florida
4) 2015 vs Florida (Butch Jones was om crack)
5) 2015 vs Oklahoma (Again Butch Jones was on crack)
6) 1993 vs Alabama (Was a tie but felt like a loss)
7) 2010 vs LSU
8) 2005 vs Alabama
9) 2008 vs UCLA
10) 2001 vs Georgia
 
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10 most painful losses in Tennessee history for me. In no particular order.
1) 2001 SEC Championship vs LSU
2) 1990 vs Bama
3) 2000 vs Florida
4) 2015 vs Florida (Butch Jones was om crack)
5) 2015 vs Oklahoma (Again Butch Jones was on crack)
6) 1993 vs Alabama (Was a tie but felt like a loss)
7) 2010 vs LSU
8) 2005 vs Alabama
9) 2008 vs UCLA
10) 2001 vs Georgia
That 2010 LSU game was brutal. As far as the worst loss I've attended, 2013 vandy sucked but the walk to the car last year after the BYU loss was awful
 
10 most painful losses in Tennessee history for me. In no particular order.
1) 2001 SEC Championship vs LSU
2) 1990 vs Bama
3) 2000 vs Florida
4) 2015 vs Florida (Butch Jones was om crack)
5) 2015 vs Oklahoma (Again Butch Jones was on crack)
6) 1993 vs Alabama (Was a tie but felt like a loss)
7) 2010 vs LSU
8) 2005 vs Alabama
9) 2008 vs UCLA
10) 2001 vs Georgia
2010 LSU was terrible. I called a friend of mine when the clock hit 0 thinking we won and in the middle of my excitement was the, "ive gotta call you back" then we lost and I never called him back. I just seen him Monday lol.

For me though, 2006 Florida was the worst for me. Had a pick 6 called back for a BS roughing the passer call and then proceeded to lose. Don't get me wrong, we still should have won, but that call still pisses me off.
 
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