Lennox Lewis - Boxing Upsets

Biggest Boxing Upsets in History

Boxing is unlike many sports in that the entire contest can be over in a flash. The history of boxing is littered with examples of boxing upsets where heavy favourites being defeated and humbled by relative unknowns or underdogs. Here is our list of some of the biggest boxing upsets in history.


  1. Breidis Prescott vs. Amir Khan (2008)

Two undefeated young fighters with records 19-0 and 18-0 respectively doesn’t feel like a boxing upset either way at first glance. Nevertheless, Prescott’s 51-second knockout of Amir Khan was so unexpected at the time that it earned the Colombian the nickname ‘The Khanqueror’. Amir Khan was a rising prospect in British boxing, and the fight was the first defence of the WBO Inter-Continental lightweight title he had won just five months before. In front of Khan’s home crowd of Manchester, Prescott landed two left hands, the first visibly wobbling him, the second putting him down. Khan made the count but never recovered and was slumped in the corner just seconds later.

  1. Frankie Randall vs. Julio Caesar Chavez (1994)

Despite being a strong fighter with a reputable record heading into the fight, Randall wasn’t thought to be a threat to Julio Caesar Chavez. Mexican sensation Chavez was undefeated in 90 fights across a 14-year professional career and was the defending WBC light welterweight champion. Most boxing upsets are the result of a surprise knockout ending the contest, but this one was a hard-fought 12-round split decision win for Randall. Chavez was also dropped for the first time in his long career during the bout which is one of the moments that defined this as such a major boxing upset.

  1. Lloyd Honeyghan vs. Donald Curry (1986)

Heading into the contest, Donald Curry was WBC, WBA and IBF welterweight champion and, after breezing through the likes of Marlon Starling, was eyeing a showdown against legendary Marvin Hagler after his fight against Honeyghan. Curry was blatant in his disregard for the threat posed by the Brit in the pre-fight press conference, but rumours were circling that he was struggling to make weight. From the opening bell, Honeyghan was aggressive and on the front foot, nearly dropping Curry in the second. Curry persisted despite being bloodied and beaten and eventually retired on his stool after the sixth.

  1. Iran Barkley vs. Tommy Hearns (1988)

Prior to this boxing upset, Hearns had only lost twice in a 47-fight career. Those defeats were against two cast iron greats in Sugar Ray Leonard and Marvin Hagler. Barkley wasn’t considered a major danger to Hearns’ run, which had seen him pick up championship belts at both middleweight and light heavyweight. With WBC middleweight title up for grabs the fight had started as expected, Hearns winning the opening two rounds comfortably and had opened up a cut which was causing Barkley issues. He looked to be on his way to a routine victory until, out of the blue, Barkley landed a right-hand counter which sent Hearns to the deck and looked to be out. Although he made the count, Barkley pounced immediately to take the TKO victory and the belt in this boxing upset.

  1. Michael Bentt vs. Tommy Morrison (1993)

In the early 90s, Tommy Morrison was touted one of the best heavyweight prospects in the business. Despite failing in his first championship attempt against Ray Mercer in 1991, he had finally managed to become a world champion in defeating George Foreman for the WBO heavyweight title. Over the space of a few months, he had already clocked up one defence against Tim Tomashek and was looking for another quick victory to set him on a path for other belts. In this boxing upset his opponent, Michael Bentt, was a relative unknown with a 10-1 record and no real victories of note. The gulf in quality between the two fighters showed in Morrison’s approach, forgoing all defence and unloading on Bentt immediately in the first round. Morrison had pushed Bentt back against the ropes, but while unleashing a barrage of punches, was caught with a thumping counter right to send him down. Failing to recover, Morrison was floored twice in quick succession to end the fight due to the three knockdown rule.

Top 10 Biggest Boxing Upsets in History

  1. Muhammad Ali vs. George Foreman (1974)

With hindsight and knowing what Ali went on to achieve, it feels counter intuitive to refer to him as an underdog prior to this boxing upset, but that’s exactly what he was heading into the ‘Rumble in the Jungle’. Foreman had captured the WBA, WBC and The Ring heavyweight belts by second round blowout against the undefeated Joe Frazier the year before and had defended twice against Jose Roman and Ken Norton. It was considered by many that Foreman’s size and punching power would prove too much for Ali. In this boxing upset it was Ali, however, who was the aggressor from the start, and his ability to avoid Foreman’s punches. Expending energy trying to hit Ali had taken its toll on Foreman and he was starting to tire, and Ali dropped him in the eighth to close off what was a stunning outcome.

  1. Evander Holyfield vs Mike Tyson (1996)

With so much controversy surrounding their rematch, it’s easy to forget how much of an upset the first fight was at the time. Despite being a former world champion and a huge name in the sport, Holyfield was on a run of 2-2 in his previous four fights, including being knocked out by Riddick Bowe just a year earlier. Tyson, on the other hand, was fresh out of prison and in one of the most intimidating and destructive periods of his career. He had captured the WBA and WBC titles in his previous two fights with crushing wins over Frank Bruno and Bruce Seldon and looked set to continue his path against Holyfield. As it transpired, Holyfield too the fight to Tyson with constant pressure and landed a left hand in the second round which staggered Tyson and he never really managed to compose himself. It went a further eight rounds but was eventually stopped in the 11th round, with Holyfield comfortably ahead on the scorecards in what was an unexpectedly dominant performance.

  1. Andy Ruiz vs. Anthony Joshua (2019)

Undefeated and carrying the WBA (Super), IBF, WBO, and IBO heavyweight belts, this was to be Joshua’s big announcement to the American market with his first stateside headline at Madison Square Garden. The preparation hadn’t gone to plan, with original opponent Jarrell Miller failing a drugs test and being replaced by Andy Ruiz Jr just weeks out from the fight. Despite Ruiz’s pedigree as a deceivingly good puncher, Joshua was still expected to put on a statement performance. He started well, and dropped Ruiz in round three which what was the first time in Ruiz’s career, but thats not what made this a shocking boxing upset. In his haste to close the contest early, AJ was clipped by Ruiz on the top of his head and dropped. After beating the count, he was felled again later in the round and started to look shaky on his feet. After scraping through the next couple of rounds, Joshua was dropped twice again, and Ruiz walked away with a shocking TKO victory and all four titles.

  1. Leon Spinks vs. Muhammad Ali (1978)

With this victorious Boxing upset, Leon Spinks became the undisputed champion of the world after just eight professional fights and would end up the only fighter to ever take a title from Ali in the ring. Ali was on the downturn of his career and after beating Earnie Shavers, he elected to fight Spinks over Ken Norton, who was chasing Ali’s WBC belt. Despite being an Olympic gold medallist, Spinks was inexperienced and hugely unfancied, but he took the fight to Ali in a way very few could have foreseen. Across 15 rounds, he was the busier and more aggressive boxer and won a split decision.

  1. James J Braddock vs. Max Baer (1935)

James Braddock is perhaps the best example of a real-life Rocky story you can find. Fighting as a light heavyweight in throughout the 1920s and 1930s, Braddock had a storied career. Following a prolific start, clocking up a record of 44-2-2 within the first three years as a professional, he knocked out prospect Tuffy Griffiths on his way to a shot against Tommy Loughran for the NYSAC, NBA, and The Ring light-heavyweight titles. Not only did he lose the fight, he also badly broke his favoured right hand, which would plague him for years to come. He subsequently went on a slide of losses and eventually, among the huge financial pressures of The Great Depression, quit boxing and worked various jobs, including as a longshoreman and at a coal yard. It appeared his career was over, but Braddock persevered and pushed and pushed his manager to get him a shot at the world title. In 1935, his opportunity arose after defeating several contenders including John Griffin and was awarded a title fight against Max Baer. Before this historic boxing upset, Braddock was viewed as a steppingstone by Baer, but Braddock shocked the world by winning a unanimous decision to become a world champion and boxing folk hero.

Top 5 Most Shocking Boxing Upsets in History

  1. Randy Turpin vs. Sugar Ray Robinson (1951)

By the time decorated middleweight champion Sugar Ray Robinson faced off with Brit Randy Turpin in 1951, he was unbeaten in 91 fights, with his single defeat in 132 overall fights was eight years before against Jake La Motta. He was on the final fight of a tour of fighting across Europe and arrived in London to collect what was expected to be a routine win against Turpin. While the Brit was certainly not on the same level as Leonard, he was strong, rough in the clinch and all round a much grittier and challenging fight than the champion expected. Turpin was warned by the referee for a kidney punch, and a clash of heads, he managed to ride out a late rally from Robinson to win on points and become the first British middleweight champion for over 60 years.

  1. Corrie Sanders vs. Wladimir Klitschko (2003)

While perhaps not yet the dominant force he would go on to be, in 2003 Wladimir Klitschko was the WBO champion, who had defended his belt five times and was widely tipped to be on a path to undisputed champion. In contrast, Sanders had a decent record, but lacked any particularly notable victories and had been knocked out by Hasim Rahman a couple of fights previous so went into this contest a huge underdog. Even with Klitschko’s inimitably cautious fighting style, Sanders didn’t take long to make an impression, dropping the champion twice in quick succession towards the end of the first round. Klitschko managed to make it to the bell, but never really recovered. Sanders swarmed him immediately from the start of the second, flooring the Ukrainian with a straight left before a final barrage caused the referee to stop the fight and etch Sanders’ name into the record books.

  1. Max Schmeling vs. Joe Louis (1936)

Ahead of their fight in 1936, Louis was hugely promising and undefeated prospect who had been tearing through the heavyweight division and many believed it was only a matter of time before he was world champion. Schmeling was a former champion but was in the latter stages of his career and his reputation with many American fight fans had been somewhat tarnished in in light of the conflicts occurring with Schmeling’s native Germany amid the build up to WW2. Louis may have been a significant favourite, but Schmeling had studied his opponent carefully and believed he had identified tendencies and opportunities to defeat the young prodigy. His homework paid off, with the German’s calculated counterpunching taking its toll and he dropped Louis in the fourth with a strong right counter. From that point, Schmeling took over the fight and battered Louis from pillar to post, eventually claiming at 12th round stoppage.

  1. Hasim Rahman vs. Lennox Lewis (2001)

Lennox Lewis only lost to two men across a glittering career that still leaves him, over 20 years later, the last undisputed heavyweight champion of the world. He lost to Oliver McCall in 1994 as WBO champion but his following 14 fight streak saw him take over the division, defeating Evander Holyfield to become the undisputed king. Since that point he had successfully defended against some dangerous foes such as Francois Botha and David Tua, who had knocked out Rahman in 1998. Rahman was considered a prospect but was having a rockier road having also been finished by Oleg Maskaev the following year and had rebuilt momentum to be back in the title frame. Going into the fight with Lewis, Rahman was a 20-1 underdog and was believed to be just another defence in the Brits’ continued dominance of the division. Once the fight started, Lewis looked a touch of pace by his own high standards, and he later admitted to overlooking the threat posed by Rahman which lead to this huge boxing upset. In the fifth round and with Lewis fighting off the ropes, Rahman landed a crashing right hand to knock the champion unconscious before he hit the canvas and send shockwaves around the boxing world.

The Biggest Boxing Upset in History

  1. Buster Douglas vs. Mike Tyson (1990)

No compilation of boxing upsets would be complete without the upset of all boxing upsets. Buster Douglas’ knockout win over a prime Tyson in 1990 remains a yardstick by which sporting upsets are viewed, boxing or otherwise. Quite simply, Tyson was a terrifying wrecking ball steaming through the heavyweight division as the undisputed champion, and Douglas was a competent but unspectacular journeyman expected to be another notch on Tyson’s considerable record. Douglas went into the fight a 42-1 underdog, with Tyson expected to make light work of the challenger as he had done his previous six title defences, all in under seven rounds. No challenger had even taken Tyson beyond the fifth round in two years, adding to the shock of this boxing upset. Despite all this, Douglas took the ascendancy from the start and utilised his reach advantage to box from the outside and nullify the champion’s offensive weapons. Tyson’s eye had started to swell shut midway through the fight and he was beginning to look completely out of ideas before he landed an uppercut in the eighth to drop Douglas against the run of the fight. It seemed as though Tyson may have finally found his rhythm and went on the attack in the ninth, but it was Douglas who bounced back to stagger Tyson and followed it in the tenth, knocking Iron Mike down for the first time in his career. The champ tried to recover, getting to his knees while trying to find his mouthpiece, but he was ultimately unable to beat the count and the referee waved the fight off for a truly shocking boxing upset.