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Boxing: The 20 Biggest Upsets in Recent History

Kevin McRaeFeatured Columnist IVJanuary 13, 2017

Boxing: The 20 Biggest Upsets in Recent History

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    Boxing is the one sport in which you can lose every minute of the contest and still come out with the victory. The one sport, where you can hit a 100-run home run in the ninth inning to win the game.

    That's why we watch. A fighter is never truly out of the fight, until that final bell rings. 

    We also watch to root for the underdog. The guy who supposedly has no shot to win but shocks the world by fighting that perfect fight or landing that one big shot.

    The following is a list of the 20 men who pulled off a feat that many felt was impossible. The 20 men who scored the biggest upsets in recent boxing history.

    A special thank you to my fellow Bleacher Report featured columnist Michael Walters, whose insight, ideas and advice were crucial to this article.

Hasim Rahman KO 5 Lennox Lewis

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    Lennox Lewis entered his 2001 fight with American challenger Hasim Rahman as a heavy favorite. He was the undisputed heavyweight champion of the world, having won that honor two years previous by defeating Evander Holyfield. 

    Since the fight with Holyfield, Lewis had made dominant defenses against extremely dangerous, at the time, challengers Michael Grant, Frans Botha and David Tua. 

    Hasim Rashman, on the other hand, seemed to be heading in the opposite direction. His only real win of note had come against the late future champion Corrie Sanders. But he had also been knocked out by heavy punchers Tua and Oleg Maskaev.

    Lewis was expected to simply walk through "The Rock" on the way to bigger and better things.

    But that's why they play the game, or in this case, fight the fight.

    As the fight began it appeared as if Lewis wasn't in the best shape of his career, he would later admit to not taking Rahman seriously enough. And in the 5th round Rahman landed a monster right hand against Lewis when he was on the ropes. 

    Lewis was out before he hit the canvas. The fight was over before the referee started the count. Lewis looked up with a dazed expression, showing he had no clue where he was and would not beat the count.

    Hasim Rahman had pulled one of the biggest upsets in history and had secured the undisputed heavyweight championship.

    The upset was so big that HBO commentators after the fight dropped comparisons to a big upset that happened in the heavyweight division in Tokyo some years before.

Evander Holyfield KO 11 Mike Tyson

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    We'll stay in the heavyweight division for our next pick.

    Evander Holyfield was supposed to fight Mike Tyson for the heavyweight title. But due to various reasons, including Tyson's prison term, the fight never took place when most felt it would be competitive.

    By the time Holyfield and Tyson signed on for their first bout in 1996, "The Real Deal" was considered damaged goods. He had recently suffered the first KO loss of his career, against Riddick Bowe, and scored an unimpressive win over blown-up cruiserweight Bobby Czyz. 

    Tyson on the other hand, had regained both the WBA and WBC heavyweight championships and appeared to be a strong and threatening as the "Iron" Mike of old. Virtually nobody was expecting Holyfield to hear the final bell, much less win the fight.

    But he did win the fight and more. "The Real Deal" dominated Mike Tyson in a way nobody had been able to do before. He bullied him, he beat him up and he stopped him dramatically in the 11th round. 

Frankie Randall SD 12 Julio Cesar Chavez

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    Julio Cesar Chavez started his career with 90 straight fights without a loss, though he did have one disputed draw against Pernell Whitaker. Nobody expected him to have trouble with Frankie Randall, who despite his impressive record was considered an easy win.

    Certainly, in the wake of the Whitaker fight, nobody expected Randall to be able to win a decision. But that's exactly what he did.

    Chavez and Randall put on quite a show with 12 competitive and hard to score rounds. Chavez was dropped for the first time in his career in the 11th round and had points deducted twice for low blows. All of these events would ultimately have a huge impact on the judges scoring.

    Randall would go on to win a split decision by judges scores of 116-111 and 114-113. The third judge had Chavez ahead by the same 114-113 score. If not for the two point deductions and the knockdown, this fight would've ended like so many others, with Julio Cesar Chavez celebrating a victory.

Bernard Hopkins TKO 12 Felix Trinidad

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    Now before you throw your arms up and say "Hopkins over Trinidad??!? That's not an upset!" Please let me explain.

    At the time of the fight, yes, it was a huge upset. Absolutely huge.

    Felix Trinidad entered the fight one of the best pound-for-pound fighters in the world. He was undefeated with 40 straight wins, huge punching power and was the overwhelming favorite to win a middleweight unification tournament set up for his own benefit.

    In his previous fight he absolutely walked through WBA middleweight champion William Joppy, a solid fighter who just got blasted out in the fifth round by Trinidad. 

    Hopkins, on the other hand, was considered by many at 36 to be on the downside of his career, how little we knew then, and had to win an ugly decision over Keith Holmes in his previous fight. 

    At the time of the fight, many expected Trinidad to knock Hopkins out. They got one half right. There was a knockout. But it was Felix Trinidad that wouldn't beat the count.

    Hopkins put on what was up to that point, and maybe even to this day, the most perfect, dominant performance of his career. This fight made Martinez vs. Chavez Jr. look like Gatti vs. Ward. 

    Hopkins won virtually every second of every round. He bullied Felix Trinidad. He beat him up on the inside and from the outside. He took him out of the fight mentally and physically. And then he closed the show with a spectacular 12th-round knockout. 

Antonio Tarver KO 2 Roy Jones Jr.

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    It wasn't so much that Antonio Tarver beat Roy Jones in May of 2004, it was how he beat him. After all, Tarver had lost a razor-thin decision to Jones in their first fight. Many felt that decision could easily have gone the other way, so it wasn't the result that was an upset. It was how we got there.

    Jones and Tarver had met the previous November. In that fight, Jones, who had just come down from heavyweight, won a close majority decision. The market for a rematch was obvious for both guys. Jones had felt he was criticized too much for winning close and Tarver felt he was robbed.

    The two signed on for an immediate rematch held in May of the following year. There would be absolutely no doubt about the outcome this time.

    Tarver landed a punch in the second round that landed like a wrecking ball on Jones' chin. The fight was over the second it connected. Tarver scored a stunning second-round knockout of the man considered one of the, if not the, best pound-for-pound fighters in the world.

George Foreman KO 10 Michael Moorer

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    Michael Moorer had won the IBF and WBA heavyweight titles from Evander Holyfield in his last fight. Looking for a high-profile name to defend against he found former champion, the then 45-year-old, George Foreman. 

    Most considered this bout lopsided as Moorer was a fast, slick, boxer and Foreman was well past his prime and had lost his last fight to Tommy Morrison. 

    And for the first nine rounds of the fight they were exactly right. Moorer boxed circles around Foreman. Foreman couldn't seem to let his hands go and when he did Moorer was already gone. Up to the 10th round it was a total mismatch.

    And then it happened. And that was the exact words of Jim Lampley calling the fight on HBO from ringside. Two of the most famous words in boxing.

    Foreman landed a hard right hand right to the jaw of Michael Moorer that dropped him to the canvas. Moorer looked up dazed before trying unsuccessfully to regain his feet. When Joe Cortez waved the fight off we heard those two famous words.

    "It happened."

    Foreman's upset was remarkable for a number of reasons. For one, he is still the oldest man to ever win a heavyweight championship. He was also 19 years older than his opponent, making it the largest gap between champion and challenger in heavyweight history. Finally, he had been dominated for the first nine rounds of the fight before hitting the lottery shot.

James "Buster" Douglas KO 10 Mike Tyson

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    In heavyweight history there was no bigger upset that this one. James "Buster" Douglas entered the ring a 42-1 underdog for the fight in Tokyo in 1990. Tyson was the undisputed heavyweight champion, an undefeated knockout machine who beat most guys before they stepped into the ring. 

    Douglas was a journeyman with a 29-4 record and had only fought for a title once, a knockout loss to Tony Tucker. To compound matters, his mother passed away during his training for the fight with Tyson, and he himself entered the ring with the flu. 

    Nobody, but gamblers looking to make a historic payday, gave Douglas any sort of chance to beat "Iron" Mike. And the story, as so many in Tyson's career, has many twists and turns.

    Douglas refused to be bullied by Tyson and wasn't afraid to let his hands go. Every time Tyson attempted to get on the inside he would pay for it. It was the first time another fighter had both the skill and the guts to stand up to the most feared man in the game.

    Douglas was winning the fight when in the eighth round he was dropped by a vicious Tyson uppercut. He rose by the count of nine, a fact that remains highly disputed to this day. Many have argued, including Tyson promoter Don King, that the count went well over nine seconds and the fight should have ended.

    But it didn't and Douglas quickly turned the tide back to his favor, punishing an extremely aggressive Tyson, who was sensing his titles slipping away, in the ninth round. By the end of the round it appeared Tyson, not Douglas, was ready to go.

    It was in the 10th round that a badly beaten up Tyson finally succumbed to the pressure. Douglas landed a huge uppercut that staggered the champ, following by several punches while Tyson was reeling that deposited him on the mat. He would not beat the count, making this one of the, if not the biggest upsets in boxing history.

Sugar Ray Leonard SD 12 Marvin Hagler

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    Marvelous Marvin Hagler contemplated retirement before "Sugar" Ray Leonard came out of retirement to face him for the middleweight championship in April of 1987.

    At the time of the fight, Leonard had been out of the ring for three years, and most considered this layoff, and Hagler's dominance, he had been middleweight champion for nearly eight years, to be too much for "Sugar" Ray to overcome.

    In the ring the pundits were once again proven wrong. Leonard boxed well, using the big ring to his advantage. He was able to keep Hagler at a distance for most of the early rounds, which he won on the cards. 

    Hagler began to close the distance in the middle of the fight and land with more frequency. One of the most hotly contested issues of the fight was Leonard's propensity to hold whenever Hagler got close. It seems like every few minutes referee Richard Steele would issue a warning but with no point deductions.

    The second half of the fight was all-action with Hagler stalking Leonard and frequently hurting him. Leonard gave as well as he got though and refused to back down. There was high drama after the final round and before the scorecards were read with many feeling the fight could go either way.

    Leonard would win the fight via split decision and scores of 118-110 and 115-113 on two scorecards. Hagler would get the nod on the third 115-113. The 118-110 card has been largely derided as too wide a margin. The outcome of this fight remains hotly debate to this day.

Leon Spinks SD 15 Muhammad Ali

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    Leon Spinks won the heavyweight championship faster than any fighter in the history of boxing. When he defeated Muhammad Ali by split decision in 1978, he was in just his eighth professional fight.

    Ali, who was coming to the downside of his prestigious career, chose Spinks because he felt he would be an easy, inexperienced opponent. He turned out to be dead wrong.

    Simply, Spinks outhustled "The Greatest." He fought every round, didn't take any time off, and made Ali keep working. And he pulled off a massive upset, defeating Muhammad Ali by split decision to win the heavyweight championship.

Michael Spinks UD 15 Larry Holmes

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    IBF heavyweight champion Larry Holmes entered his fight with Michael Spinks on a 48-fight winning streak. Spinks, the reigning light-heavyweight champion, was a heavy underdog and most felt he would not be big enough to stand in there with the hard-hitting "Easton Assassin."

    Spinks was able to use his considerable speed advantage to outbox Holmes over 15 rounds. It was a very close fight, and a decision that Holmes hotly disputed. 

    When the scorecards were read, Spinks won a unanimous decision by scores of 145-142 twice and 143-142. He would become the first reigning light-heavyweight champion to win a title at heavyweight. He would go on to defeat Holmes a second time in a rematch, another close, and disputed decision.

Lamon Brewster TKO 5 Wladimir Klitschko

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    Few people had even heard of Lamon Brewster, much less gave him a shot, when he traveled to Germany to challenge Wladimir Klitschko for the vacant WBO heavyweight championship.

    And after four rounds it didn't appear that we would ever hear from him again. Wladimir unleashed a hellacious assault on Brewster culminating in a fourth-round knockdown. But Brewster was able to withstand the assault, leaving Wladimir seemingly out of gas in the fifth. 

    Brewster began backing up the bigger man with hard shots and forced a standing eight count when he battered his foe along the ropes. Klitschko was out on his feet and collapsed to the canvas after the bell for round five prompting the referee to stop the fight. 

    It was a massive upset and one that seemed all the more improbable after the four-round beating endured by Lamon Brewster.

George Foreman TKO 2 Joe Frazier

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    George Foreman was a feared power puncher and used his strength and size to bully and dominate his opponents. But he wasn't very fast and many areas of his game were very raw. Joe Frazier felt he would be the perfect opponent for his style.

    It didn't quite turn out that way in the ring. Foreman used his size and strength to dominate the undefeated heavyweight champion. Frazier was knocked down three times the first round, and three in the second round before the fight was stopped.

    Foreman's victory would pave the way for another big upset.

Muhammad Ali KO 8 George Foreman

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    Context is key here, before you go off and say "wait, how could Ali upset anybody?" Well he could, and he did in The Rumble in the Jungle.

    Ali entered the fight with Foreman, after "Big" George had just blasted out undefeated heavyweight champion Joe Frazier in two rounds and did the same to Ken Norton.

    Ali, many felt, would struggle with Foreman's size and power. Most expected him to try and stay outside and outbox the bigger man, using his speed and reflexes to avoid George's power. 

    But that's not how it went down. Ali was very aggressive early in the fight, fighting, rather than boxing Foreman. Starting in the second round, he would sit back on the ropes and allow Foreman to unload. Many of the shots were deflected or blocked. 

    The strategy, later called "rope-a-dope" exhausted Foreman. He expended so much energy and barely landed anything damaging to Ali. He was primed for a major fall, and that's what happened when Ali dropped him and stopped him in the eighth round. It was a stunning upset, especially given how it went down.

Iran Barkley TKO 3 Thomas Hearns

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    Iran "The Blade" Barkley wasn't given much of a shot of beating  Tommy Hearns when the two stepped into the ring for a middleweight title fight in June of 1988. 

    Hearns' only losses had come against Marvin Hagler and Sugar Ray Leonard and he held victories over Wilfred Benitez and Roberto Duran. Barkley didn't have anything close to that on his resume.

    In the third round, Barkley, who had lost the first two rounds and was badly cut, dropped Hearns with a huge lunging right hand. He was able to get up but was clearly out on his feet. "The Blade" followed up by knocking Hearns into and through the ropes for the stunning TKO victory.

Corrie Sanders TKO 2 Wladimir Klitschko

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    Wladimir Klitschko is in the unenviable position of appearing on this list twice. His stunning defeat against the late Corrie Sanders took place nearly a year before his defeat by Lamon Brewster but was even more shocking.

    Sanders did not hold any victories of significance and had been knocked out two fights prior by Hasim Rahman. 

    Wlad on the other hand was the WBO champion and widely considered the most dominant force to hit the heavyweight division in years. 

    The fight didn't last long. Sanders came out highly aggressive and dropped Klitschko with under a minute left in the first round. He was able to get up but was quickly dropped a second time before the round ended.

    Knowing his opponent was badly hurt, Sanders went for broke at the start of the second, landing a huge straight left that caused a third knockdown. Sanders pounced once Klitschko rose to his feet and landed several huge shots prompting the justified stoppage. 

    Sadly, Corrie was taken from us under tragic circumstances earlier this year. But this upset will live on for a long time.

Michael Bentt TKO 1 Tommy Morrison

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    Tommy "The Duke" Morrison was once considered one of the biggest can't miss heavyweight prospects in boxing. While he lost his first challenge for a world title, by eighth round TKO against Ray Mercer, he was successful in his second attempt. He defeated George Foreman by unanimous decision to win the vacant WBO title in 1993.

    Morrison successfully defended the title in his next fight against an unheralded opponent and was set to do so again against Michael Bentt, who was a virtual nobody with a 10-1 career record and zero notable wins.

    Morrison went on the attack early in Round 1 and unloaded on Bentt against the ropes. Morrison let his hands go with total disregard for defense, firing wide, winging shots. And he got caught with a huge right hand that changed the fight on a dime.

    Morrison was badly hurt and Bentt was able to follow up and drop him. It was now Bentt on the attack, landing huge shots that deposited "The Duke" on the mat a second time. With the three knockdown rule in effect, all it took was one more big shot to end the fight.

    And Bentt quickly got it, landing a huge uppercut along the ropes that put Morrison on the mat for the third and final time. With the victory, he became perhaps the most unknown heavyweight champion in history. He would lose the belt in his next fight, and retire with an 11-2 overall record.

Carlos Baldomir UD 12 Zab Judah

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    For Zab Judah, it was simple heading into his fight with journeyman Carlos Baldomir at Madison Square Garden. Judah was the undisputed welterweight champion, and a win would secure a huge fight with Floyd Mayweather Jr.

    Judah was super-confident heading into the fight, and tried to force his opponent off his game when he threw a low-blow, during the pre-fight instructions.

    But while Judah would ultimately get the Mayweather fight anyway, he would not get past the rugged Argentine Baldomir.

    The fight was close early, with Baldomir putting a great deal of offensive pressure on Judah. As the rounds went on, the pressure continued, but Judah appeared to be doing less and less. When the cards were read after the 12th round, it appeared that the chance of a Mayweather-Judah fight was DOA.

    Baldomir won unanimously by scores of 115-112, 114-113 and 115-113. With the win, he secured the WBC and The Ring Magazine titles. He did not take Judah's WBA and IBF belts because he refused to pay the sanctioning fee and those belts were not on the line.

    The fight was declared the 2006 upset of the year by The Ring Magazine.

Ricardo Mayorga TKO 3 Vernon Forrest

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    The late Vernon Forrest was the best kept secret in boxing for years. That secret exploded on the scene when Forrest dominated and defeated the previously undefeated Shane Mosley in 2002. He followed it up by defeating Mosley again in a rematch and was now himself considered the man at welterweight.

    Ricardo Mayorga was a raw, reckless power puncher. He did hold a victory over Andrew Lewis and had 21 knockouts in 23 wins but was considered tailor-made to be picked apart by Forrest.

    Mayorga, as was his custom, came out swinging with Forrest trying to control distance and box. In the final seconds of the first round, Mayorga landed a huge, looping hook that stunned Forrest and then dropped him to the canvas.

    Forrest came out much more aggressive in the second round, abandoning boxing and playing right into Mayorga's hands. Forrest was able to land some huge shots of his own but Mayorga took them well and returned fire.

    At the end of the second round, Larry Merchant described the bout as a street fight, and that's exactly what it turned out to be.

    Mayorga didn't change a bit at the start of the third round, landing huge shot after huge shot. With just over a minute left in the round, Mayorga landed a left hand that staggered Forrest into the ropes and then a huge right that put him down.

    Forrest rose to his feet but was on wobbly legs, and had a glazed, vacant stare on his face. This prompted referee Marty Denkin to stop the fight. 

    And it led to one of the most interesting moments in boxing, when Larry Merchant provided Mayorga with a cigarette to smoke to toast his victory.

Vince Phillips TKO 9 Kostya Tszyu

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    Kostya Tszyu entered his fight with "Cool" Vince Phillips as a huge favorite. He was undefeated, held the IBF junior welterweight title and had huge knockout power.

    Phillips had been a good contender for a number of years but was looking a bit shop-worn and had dropped a decision in his last fight against the anonymous Romallis Ellis. 

    It was considered by most to be a soft-touch for Tszyu. It turned out to be anything but. 

    Phillips pressured Tszyu and the two engaged in many notable exchanges. The fight was toe-to-toe an extremely close entering the ninth round, when just over a minute in, Phillips landed the shots that rocked, hurt and ultimately stopped Tszyu's undefeated streak.

    Phillips forced Tszyu along the ropes and unleashed hell. He landed several clean, hard shots that had his opponent out on his feet. Nothing was holding him up but the ropes and the stoppage was totally justified.

James Toney TKO 11 Michael Nunn

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    Michael Nunn was 36-0, considered one of the best fighters in the entire sport and the IBF middleweight champion.

    James Toney, though undefeated, was little known and given little shot to upset Nunn. It was expected to be a prototypical hometown fight for Nunn, with the ending being an impressive victory.

    The pre-fight hype was intense with both fighters making controversial and inflammatory remarks about the other. Threats were common and none was better than when Toney threatened to "break his bones."

    The fight started exactly as most felt it would, with Nunn jabbing to get inside Toney's defense and then landing hard combinations. At the midway point of the fight, it appeared that he was heading towards a satisfying victory in front of his hometown crowd.

    Toney changed his strategy at this point and began going to the body. He was able to land more punches and did better, but with all the early rounds seemingly in the bank for Nunn, he was going to need to do something dramatic to win.

    And he did just that. Toney was suddenly able to land huge, powerful shots that rocked and hurt Nunn. With just over a minute left in the 11th round, he landed a massive left hand that dropped Nunn and, for all practical purposes, ended the fight.

    Nunn rose to his feet but was clearly out of it. Toney pounced and forced Nunn into the ropes, throwing wild shots and eventually connected on a right that sent Nunn down again prompting the stoppage.

    Toney was way behind on all the cards and seemed headed for defeat before scoring one of the most impressive and stunning knockouts in boxing history.

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