Best Boxing Upsets Of The Past Twenty Years

Number 6: Marco Antonio Barerra puts on a clinic against undefeated Naseem Hamed in 2001. Result: 115-112, 116-111 and 115-112, all for Barerra.

Barerra came in to this fight as a “washed-up” 27-year-old who was recently beated badly by Junior Jones twice via a fifth round retirement and decisive UD 12 loss. He shot back up on the boxing scene after giving the undefeated Erik Morales all he could handle in 2000, even knocking the champion down in the 12th and final round in which Barerra would lose a close split-decision.

Hamed was an exciting brawler and laughably was seen as the most powerful puncher in boxing, despite weighing only 126 pounds. Hamed was a showman, never lost a fight and put on a long ring entrance that angered Barerra, as well as the fans.

What ensued when Hamed stepped in to the ring was utter choas to this writer. Marco didn’t have a chance, did he?

Barerra proceeded to defy the critics, and stuck to boxing circles around Hamed. Hamed did virtually nothing the first seven rounds, and was down big before he landed a couple straight right hands to Barerra’s nose.

Barerra landed many shots that whipped Hamed’s head back, bent him at the waist and nearly floored Hamed a few times.

To solidify and puncuate his upset of Hamed, Barrera even slammed the Englishman’s head in to the turnbuckle in the 12th round. What a fight! No controversy, just an utter upset!

Number 5: Bernard Hopkins TKO 12 Felix Trinidad in 2001. Felix Trinidad was seen as a force in the early twenty-first century. He had defeated Oscar De La Hoya and took his WBA and WBC welterweight belts in 1999. He had engaged David Reid in early 2000, knocking him down five times and taking his WBA light middleweight belt and winning a UD by seven points!

Trinidad unified the titles by tussling with Fernando Vargas in a classic duel that ended with Vargas being knocked down twice in the first and three times in the twelfth despite making it a competitive bout.

Hopkins was just a quiet fighter as well as a middleweight champion. He had defended his portion of the middleweight championship for the better part of seven years, never tasting defeat since Roy Jones beat him in 1993.

Don King would coax Trinidad to keep moving up, despite knowing that the Puerto Rican star had been down in successive fights. Reid knocked him down in their fight at 154 and Vargas did as well.

So, Trinidad took on William Joppy for the WBA version of the middleweight championship and starched Joppy in five lopsided rounds. This was part of Don King’s historical middleweight tournament in which Hopkins had dominated Keith Holmes for the IBF and WBC titles.

Don King wanted to make Felix Trinidad a legend; Bernard Hopkins had other plans.

The fight was postponed due to the terrorist attacks in New York City. Hopkins had stepped on the Trinidad’s home flag, but the two became a symbol for the country to take our minds off of tragedy.

The bout was electric, the national anthem was stirring. I literally had tears in my eyes. All of the sudden, Trinidad was human. Bernard Hopkins would put on one of the most inspirational performances of the last thirty years.

Here was a convict, on America’s darkest time, living the American Dream! He was imprisioned for 56 months, didn’t start boxing until he was 23; had no chance, you say?

Trinidad had no respect for Hopkins’ power from the outset. He began eating heavy leather as he was trying to walk through the stronger Hopkin’s shots. Hopkins lost the first round and would began to dominate every round since.

Trinidad was given false hope by his trainer/father because he told Felix he was winning every round. Hopkins began to muscle Trinidad, humiliate him and even taunt the three-division champion.

What was happening? For every big shot Trinidad threw, Hopkins would smile at him, smile some more, and give one back harder than he took one. The 36-year-old Hopkins was turning back the clock.

There were flurries, especially the sixth round. There was action and there was heart for the fading Trinidad. He was losing badly on HBO’s unofficial judge Harold Lederman’s card heading into the 12th by a score of 108-101.

Trinidad kept coming forward, Bernard finally put him away. In what was a classic fight, it was also unusual due to the fact that it was such a domination. This fight remains a classic in this writer’s eyes.

Number 4: Bernard Hopkins stuns Antonio Tarver, climbs two divisions to capture Ring Magazine 175 lb title belt in 2006.

This was supposed to be a walk-over for Tarver, who was coming off two victories over Roy Jones as well as a part in the new “Rocky Balboa” movie.

Hopkins was again an underdog and had even hired strength trainer Mackey Shilstone to get him in shape for the bout, making sure he wouldn’t lose any speed or power.

This fight would not even be close, Hopkins would score a knockdown and rip Tarver’s belt away in dominating fashion. Judges could only give Tarver two rounds.

Tarver came in out-of-shape and virtually did nothing the entire fight. Hopkins remains a timeless classic.

Number 3: Evander Holyfield stuns Mike Tyson by TKO 11 in 1996. Evander Holyfield entered the fight as a massive underdog, no one picked him to get past the first. But what Holyfield did was capture the hearts of millions in 1996 and put a huge dent on Tyson’s post-imprisonment plans for an undisputed heavyweight championship.

Tyson had picked up scraps by feasting on the weaker Frank Bruno and Bruce Seldon before the fight with the fading Holyfield.

I remember when my parents used to work at a group home for boys in the 1990’s in Hermitage, PA and seeing Tyson when he wanted to speak to the troubled boys my parents were supervising.

I always thought the world of Tyson, seeing him in person does him justice. In what many see as a tortured soul, I saw as a kind man – albeit with flaws – but he was pleasant to be around. After Tyson blitzed McNeely, he allowed me and my cousin to ask him questions. He answered, and even signed autographs for us.

I still have that picture with him while I was a pudgy, twelve-year-old kid and had the biggest smile on my face. Mike Tyson was larger-than-life. Even when he was released from prison, he still had his fans and his life. This saddens me because this fight marked another downward trend in his career as well as his personal life.

Holyfield was also a great fighter. He was an Olympic Gold Medalist, a religious man that had many endearing qualities. Holyfield had a heart condition that dimmed his record as he lost to Riddick Bowe by a knockout due to fatigue and an upset loss to Michael Moorer.

Tyson was a huge favorite, I think it was 35-to-1, not quite sure. Tyson had started out strong and landing flurries that wobbled Holyfield in the early going. Holyfield would pick up steam and began to wear Tyson down.

What was shocking was the fact that Tyson looked physically inferior to Holyfield. Tyson would eat straight right hands all night as well as the occasional uppercut or headbutt, depending on what corner you interview.

Simply, Tyson was spent by the 11th round. He would get knocked down in the eleventh round and referee Mitch Halpern would step in and stop the fight with no count at all.

Tyson was lucky if he won two rounds in this fight. It was sad considering how much prison had eroded his skills as well as pulling the “wool” over all of his fans eyes by thinking Tyson would always be the same dominating force.

Number 2: Hasim Rahman KO 5 Lennox Lewis. In what was supposed to be a “walk-over” for Lennox Lewis, he came in overweight and out-of-shape.

He took the fight in South Africa and did his physique no favors due to the high-altitude. Lewis was dominating early, picked up three of the first four rounds using his jab, but let himself be pounded by a right hook that came out of nowhere by the little-known Rahman.

Rahman was all smiles, even summed up the post-fight analysis by saying, “That punch was rated-R”.

Number 1: Buster Douglas TKO 10 Mike Tyson, 1990. I remember seeing this fight on a replay when I was seven. I thought I was seeing an alternate universe.

The fight was on a delay from Tokyo, Japan and Douglas was a 42-to-1 underdog as was seen as a tune-up for Tyson. Tyson, to his credit, actually never took Douglas seriously, but when I see replays of this fight, I always expect it to end differently-and-it never does.

Douglas had an overwhelming reach advantage to Tyson’s short, yet massive arms. Tyson was being hit by overhand rights the whole night, but kept coming forward. He came in, won a few rounds and kept Douglas wary of his power.

By the eighth, Tyson was losing and even put Douglas down. I always review this portion of the fight because it has become a summary of Tyson’s career. I actually do think that Douglas was down for ten seconds, but was allowed to continue!

This “second chance” allowed Douglas to continue his composure. By the ninth, Tyson was tiring and on wobbly legs, even stunned at the end of the ninth round.

Then came the tenth and fateful round.

Douglas punished Tyson like he stole something as Tyson was nailed with a series of lefts and rights that put him down. Tyson went down and was so concerned with putting his mouth-piece back in because he was knocked cold.

Tyson never got his mouthpiece in and never got up. He was counted out. A huge upset in boxing history and perhaps the greatest of all time.

This is very saddening considering that Tyson was a brutal force that many saw couldn’t be beaten. A “swarmer” that made opponents pay, Tyson went to prison and began to unravel.

Douglas won the fight for his deceased mother and never really did anything after he beat Tyson.