Most gut-wrenching loss as a fan.

[dajuggernaut]

Winky Wright beating Felix Trinidad.

This is a summary of the bout.

Also Paul Williams losing to Sergio Martinez but that had to do with money.

[SaadOffTheDeck]

Holyfield/Bowe 1 & Hearns/Hagler.

[allworld80]

It's too gut wrenching to talk about, sorry.

[NazNaci1]

It's too gut wrenching to talk about, sorry.

Holyfield v Tyson I - I was a fan of both, so one had to lose.

[Goodnight, Irene]

I'll never forget De La Hoya-Pacquiao. That takes the cake.

Watching Oscar lament, "Well...my heart still wants to fight," into Larry Merchant's microphone was wrenching.

[jaclem2]

charles/walcott III.....charles marciano I

[Ezzard]

Seeing McGuigan storm back from a fight he was losing only to get dropped multiple times in the last round...

[Roars Like Me]

It's too gut wrenching to talk about, sorry.

Ahem its is Zoo/Hatton per chance?

[Goodnight, Irene]

It's too gut wrenching to talk about, sorry.

Ahem its is Zoo/Hatton per chance?

You are not a true boxing fan unless you can spell his name

[Roars Like Me]

It's too gut wrenching to talk about, sorry.

Ahem its is Zoo/Hatton per chance?

You are not a true boxing fan unless you can spell his name

Tut tut back at you ol' bean, you must have seen it spelt like that before? 'tis the norm for peeps in the know
I am aware it's Tszyu

[Seamus]

Barry McGuigan to Steve Cruz
Sugar Ray Leonard to Norris and Camacho

[wsbuf]

Mancini-Bramble
Ali-Spinks

[raylawpc]

Except for the time he beat Ron Lyle, every time Cassius Clay/Muhammad Ali won was pretty gut-wrenching for me.

[Counter-puncher]

Chavez losing to DLH

McGuigan - Cruz is a good shout.

Gary Mason losing to Lennox Lewis affected me strangely at the time.

[gilgamesh]

Castillo vs Corrales 1 was gut wrenching for me as Castillo was definitely one of my favorite fighters at the time, and aside from that I'd been picking Castillo to win via 10th round KO the whole month leading up to the fight, and just as it seemed as though I was right, I had called it right on the money Castillo is moments away from scoring his 10th round KO, Corrales hurts him launches an assault on the ropes and I see Tony Weeks waving off the fight and Corrales being declared the winner, I was in such a state of disbelief I was speechless for at least 5 minutes.

[turn2stone]

ali-holmes was pretty sad.

i was a teenager and got caught up in the media hype of ali actually having a chance.

in hindsight it was pathetic. and laughable that i'd actually believe that sort of act.

knowing now about the obvious brian damage ali was already suffering etc just adds to the slimy feeling of this bout that should never have happened.

[SaadOffTheDeck]

Castillo vs Corrales 1 was gut wrenching for me as Castillo was definitely one of my favorite fighters at the time, and aside from that I'd been picking Castillo to win via 10th round KO the whole month leading up to the fight, and just as it seemed as though I was right, I had called it right on the money Castillo is moments away from scoring his 10th round KO, Corrales hurts him launches an assault on the ropes and I see Tony Weeks waving off the fight and Corrales being declared the winner, I was in such a state of disbelief I was speechless for at least 5 minutes.

You predicted it exactly right. Without the sissy mouthpiece crap, Chico would have never made it. Still amazing that he came back, but a tainted win all the same. I never forgave corrales for that. So yeah, that one hurt me too.

[Goodnight, Irene]

Seeing Hatton Ko'd as brutally as he was by Pac tied my stomach in knots.

It was a tentative decision, but I backed Hatton. Thought he would be hungry as to beat a name as big at the time as Pacquiao.

The KO shot was simply a sensation. Many felt Hatton was dead.

[Goodnight, Irene]

Certainly not. I cannot decide, looking back, if the performance which really left me struggling to explain his freakish brilliance (at the time, & in the moment) as a fighter was either the shut-out stoppage of De La Hoya, or the complete annihilation of Hatton. Both left me truly stupified.

[Deno1986]

Seeing McGuigan storm back from a fight he was losing only to get dropped multiple times in the last round...

This would be my pick aswell. Although I wasn't around when the fight was on, it was agonising watching it a few years ago. I wouldn't be able to bring myself around to watching it again despite it being a fantastic fight.

[SaadOffTheDeck]

I liked barry as well, Duran lost a razor close decision to Hagler's half brother in the next fight before Hearns averted a complete disaster in the Main. That was like a $19.95 PPV.

[Knucklez]

I was 12 when Tyson fought Buster Douglas in Japan. Tyson at the time was like a god to me as I was probably too young to understand all of his...extra curricular...problems.

Seeing him get battered all over the ring and then KTFO was truly devastating and I still hate watching that fight! Hagler-Leonard still smarts too.

I would also add in Herol Graham's devastating loss to Julian Jackson. A punch-perfect performance ended with one dynamite right hand to the chin. The British commentator was equally as upset: "Oh noooo!" with the assistant commentator calmly adding "he's out."

[allworld80]

It's too gut wrenching to talk about, sorry.

Ahem its is Zoo/Hatton per chance?

Yes, and I haven't had another "favorite" fighter since, just so I wouldn't have re-live that feeling.

I am partial to JMM these days though. Brilliant offense, and just enough holes in his defense to make his fights competitive.

[gilgamesh]

Castillo vs Corrales 1 was gut wrenching for me as Castillo was definitely one of my favorite fighters at the time, and aside from that I'd been picking Castillo to win via 10th round KO the whole month leading up to the fight, and just as it seemed as though I was right, I had called it right on the money Castillo is moments away from scoring his 10th round KO, Corrales hurts him launches an assault on the ropes and I see Tony Weeks waving off the fight and Corrales being declared the winner, I was in such a state of disbelief I was speechless for at least 5 minutes.

You predicted it exactly right. Without the sissy mouthpiece crap, Chico would have never made it. Still amazing that he came back, but a tainted win all the same. I never forgave corrales for that. So yeah, that one hurt me too.

It took me like 2 weeks to except what had happened and I agree with Castillo's sentiments that Weeks should've stopped the fight after Corrales went down the 2nd time, but I suppose if that had happened then it wouldn't be remembered as one of the best fights of the decade.

[Norm]

Arguello vs Pryor 1 was the worst one for me. Panama Lewis was able to revive Pryor's energy in amazing ways between rounds that led to a brutal beating for Alexis.