Most embarassing losses...

Bert Cooper quitting against George Foreman. The Crack was calling him back to the hotel room. He said he was up 3 days straight before the fight Smoking Crack then says In the post fight interview that Foreman hit too hard and Bert didn't want "brain damage".

Terry Norris getting KOd by Simon Brown in Mexico. There were some things that went on previous to their fight. Simon pulled out of a Norris fight because he felt something was wrong with his heart. (Medically)

So Norris played the classic bully accusing Brown of being scared of him.
That is one of my favorite.

 

Duran loses to Laing,,,that one is a yardstick to measure the rest by

 

Witherspoon-Bonecrusher II

Carl Williams - Mike Weaver
John Tate -Weaver
Lonnie Beasley - Charles Brewer
Huge Gerry Cooney being decimated by li'l Michael Spinks

 

Even tho he was past prime and over his best weight I am having a hard time thinking of a better one than this in the more recent times.

For olden days I would say Dempsey getting flattened by a losing streak Flynn or getting clowned by a fat nobody in Willie Meehan.

 

Bramble vs. Rosario. The tough Bramble who said he could not be knocked out is destroyed rather easily by Rosario. Almost an outclassing. I don't think Bramble landed one clean punch on Rosario.

 

Boone Kirkman getting KTFO cold by "Memphis" Al Jones. . . . . Boone was ranked #7 and was taking a tune up fight versus Jones while awaiting a NABF title fight against Muhammad Ali in Kirkman's hometown of Seattle.. Boom Boom's only losses previously were to Doug Jones on cuts and to George Foreman and had won 10 straight fights leading to the Memphis Al fight in their April of 1974 match. In the bout Kirkman had dropped his opponent 4 times in the first three rounds before a thundering overhand right came out of nowhere to crash on Boone's jaw and end the scheduled payday against Ali.. . . .Boone had a record of 33-2 going into the fight and afterward lost three consecutive fights thus knocking him forever out of any consideration of further boxing glory.. . . .Later his notoriety came as part of the "Toronto Five" and then his last boxing appearance came against Gerry Cooney in a 1983 exhibition at Eugene, Oregon

 

Gatti & Ortiz vs Mayweather
Linares vs Salgado
Malik Scott vs Wilder
Roy Jones Jr & Briggs vs Danny Green

 

I think this is the greatest upset in history, but embarrassing ? Douglas fought a helluva fight.

 

It was embarrasing because nobody gave him a chance and the way he beat Tyson was humiliating specifically since Tyson was seen as unbeatable up till that point.

 

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I was going to add this one. If theirs a such thing as Karma or comeuppance Hembrick certainly got his in spades..... And deservedly so. One of the most pleasing results I've seen in a professional fight.

 

Ali losing the belt to a man with less than 8 fights
Leonard trying to come back against Camacho
Hopkins getting blasted out of the ring by Smith
Khan getting blitzed by Prescott

 

Larry Donald was even worse since he was a past his prime gatekeeper. Holyfield didn't even win a single round. Even a 2001 Holyfield would've beaten Donald by a decision.

 

Holyfield getting stopped by fat Toney.

 

Vitali Klitschko vs Chris Byrd - A 6'8 SHW quitting against a fat MW because he hurt his shoulder

Roy Jones vs Glen Johnson - Roy getting KO'ed by a guy he would have schooled in his prime, suppose you could say the same about the Tarver KO

Danny Williams vs Vitali Klitschko - Danny was never in Vitali's league but all the extra weight he had gained meant he could barely move, a total mismatch which was painful to watch