Top 10 Most Expensive Knockout Upsets in Boxing

Former undisputed heavyweight champion of the world Mike Tyson once said, “Everybody has a plan until they get punched in the face.” That’s something he probably learned through experience. After all, even Iron Mike himself has been on the receiving end of a punch in the face that stopped him cold in his tracks. In fact, every boxer, save the rare few who went undefeated throughout their entire careers, have experienced the same.

Perhaps that’s part of what makes the sport of boxing so exciting. No matter how heavily favored one boxer is over another, there’s always the chance that the underdog can sneak in a lucky one that could win him the whole fight. And it’s happened quite a number of times in boxing history: a heavy favorite goes into a fight expecting to tuck an easy win under his belt only to find himself knocked out by an unheralded fighter.

The list that follows is composed of bouts in recent history (70s onwards) that stunned the boxing world. Matches that ended with highly favored boxers being knocked out were selected because they, rather than fights that ended in decisions, were the ones with the most shock value. Furthermore, the list is arranged in terms of the disparity between the purses of the two fighters (adjusted for inflation) since it’s a common practice in boxing to pay the more highly touted boxer a bigger share of the purse than the perceived underdog. Thus, the greater the fight purse disparity, the more shocking the upset supposedly is.

10 Muhammad Ali KO8 George Foreman (October 30, 1974) / Fight Purse Disparity: $0

Yes, they may have both been huge names in boxing, and they may have received the same amount of money for the fight, but Muhammad Ali knocking out George Foreman in 1974 was definitely a huge upset because of its context.

"The Rumble in the Jungle", which was one of the first ventures of famous promoter Don King, was quite heavily lopsided in favor of Foreman because Ali, at that time, was still searching for redemption. "The People's Champion" had been suspended from boxing for 3 and 1/2 years due to his refusal to enter the U.S. Army after being drafted. Then, when he finally secured a heavyweight championship fight against Joe Frazier in "The Fight of the Century", Frazier scored a unanimous decision, leaving Ali fighting other contenders to try and get a new title shot. Meanwhile, Foreman was 40-0 with 37 knockouts, one of them being against Frazier and another being against Ken Norton, the only man besides Frazier to have beaten Ali at that time.

Come fight day, Ali decided to employ what is now known as the "rope-a-dope" strategy. It involved staying close to the ropes, absorbing Foreman's attack, then countering with pinpoint punches to the head. All the while, Ali taunted Foreman to punch harder by hurling lines like "Is that all you got, George?" and "They told me you could punch!" The harder Big George tried to hit, the quicker his gas tank emptied, eventually allowing Ali to deliver a five-punch combo that knocked the champion out and shocked the boxing world.

9 Lamon Brewster TKO5 Wladimir Klitschko (April 10, 2004) / Fight Purse Disparity: $370,000

Describing his fight against the younger of the Klitschko brothers, American Lamon Brewster recalled, "It was kill or be killed." Usually, talk like that can be dismissed as usual meaningless boxing banter, but getting killed was a very real possibility for Lamon in his meeting with Wladimir against whom Brewster was supposedly grossly mismatched.

The fight was for the vacant WBO heavyweight championship, and after the first four rounds, it looked like the favored Ukranian was living up to his nickname, "Dr. Steelhammer". He peppered Lamon with power punches that culminated in a fourth-round knockdown. Brewster was able to get up though, and in the fifth Klitschko looked exhausted from the previous round's effort. Lamon, on the other hand, considered it his opportunity to deliver some heavy punches of his own, in the process flooring Wladimir. The Ukranian couldn't get up and Brewster shockingly won the championship.

After the fight, Klitschko expressed that he believed he had been drugged after the opening round. His blood and urine samples taken after the fight were allegedly missing, and suspiciously, the odds favoring Wladimir had dropped significantly before the fight.

8 Lloyd Honeyghan TKO7 Donald Curry (Sept. 27, 1986) / Fight Purse Disparity: $506,000

The Monday morning after the world welterweight title fight in September of 1986, the Daily Mirror headline blared, "THE MAN WHO SHOOK THE BOXING WORLD". The boxer referred to was Lloyd Honeyghan, who despite his stellar 27-0 record and European, British, and Commonwealth championships, was so unheralded that many oddsmakers refused to issue a betting line for the fight. The reason why the fight seemed like such a mismatch was that Donald Curry was the first undisputed welterweight champion since Sugar Ray Leonard, and his 25-0 record included 20 wins by knockout.

Come fight time, however, it was Honeygan who looked more like a champion, dancing around the ring in his purple sequined shorts, while Curry looked quite lethargic. And by the seventh round, it was all over; a cut under Don's left eyebrow, which had been opened by an accidental head butt in the fifth, was deemed by ringside doctors to be too ugly. Lloyd had done it: he had won the WBA, WBC, and IBF Welterweight Championships in a stunning upset. And by TKO, too.

7 Corrie Sanders TKO2 Wladimir Klitschko (March 8, 2003) / Fight Purse Disparity: $506,000

This match was supposed to be a "stay busy" fight for Wladimir Klitschko, who was very much expected to defend his WBO Heavyweight Championship against Corrie Sanders, a boxer who had been coaxed out from retirement and had been working as a pro-golfer in his native South Africa.

Right at the beginning of the fight, Sanders came out aggressively and exchanged punches with the champion. However, it was Corrie who was doing the real damage, a vicious left knocking Klitschko down with 35 seconds remaining in the first. In fact, Wladimir barely got up as the referee reached the count of eight. Then in the second, Sanders charged like a bull and felled Klitschko once more with another left just seven seconds into the round. Again, the champion got up only to be overwhelmed by a barrage of punches that sent him to the canvas one last time.

Corrie was tragically killed in a robbery in 2012. The Klitschko brothers released a statement saying they would remember the late boxer "as a great person both inside and outside the ring".

6 James Toney TKO11 Michael Nunn (May 10, 1991) / Fight Purse Disparity: $744,000

Before his sixth IBF Middleweight title defense, Michael Nunn, with his record of 36-0, was irritated by James Toney's trash talking. James, although a huge 20-to-1 underdog despite being undefeated, threatened Michael that he would "break his bones" during the fight. Nunn responded by vowing, "I'm going to punish him. I'm going to enjoy punishing this guy."

Well, after five rounds, it appeared that Nunn would keep his word. He fought brilliantly and jarred the challenger with fierce combinations. Toney, meanwhile, had other ideas. He told his corner, "He's tiring. I can hear him breathing like a freight train. I'm going to step up the pressure." And by the eighth, Nunn did indeed appear gassed and was getting hit by James. "He's not hurting me," Michael defiantly declared.

However, a minute into the eleventh of the scheduled twelve-rounder, Toney hit Nunn with a right to the head that caused the champion to drop his hands and get bombed with a left hook that violently snapped his head sideways and put him on his back. Michael stood up to the count of nine only to catch two more right hands from James, causing a white towel to come flying into the ring from Nunn's corner.

5 George Foreman KO10 Michael Moorer (November 5, 1994) / Fight Purse Disparity: $6.29 Million

Michael Moorer had won the IBF and WBA Heavyweight Championships from Evander Holyfield and was looking for a high-profile name to defend his titles against. When he picked George Foreman, who was then 45 years old, the boxing world shook their heads in disappointment since "Big George", although on the comeback trail, was already past his prime.

For the first nine rounds, the 3-to-1 betting favorite pummeled Foreman, who couldn't seem to throw his punches. And then, in the tenth, George shockingly landed a hard right to the jaw that dropped Moorer to his feet. That caused Jim Lampley to utter the two most famous words in boxing: "It happened."

By knocking out Michael, Foreman became the oldest man ever to win a heavyweight championship. The gap of nineteen years between champion and challenger was also the largest in heavyweight history.

4 Evander Holyfield KO11 Mike Tyson (November 9, 1996) / Fight Purse Disparity: $7.42 Million

This is the one before the infamous ear-biting fight that took place seven months later in 1997. In this initial encounter, Evander Holyfield was a 25-to-1 underdog because he had previously suffered the first knockout loss of his career against Riddick Bowe before scoring an unimpressive win over Bobby Czyz. "Iron Mike", on the other hand, had regained both the WBA and WBC Heavyweight Championships and was looking like the Tyson he was before his prison sentence. In fact, the match was deemed so lopsided that the question being asked wasn't whether Holyfield would win or lose; it was whether he would live or die.

Against expectations, after a close first round, Evander jerked Tyson's head from side to side with a series of blows, and everything proceeded to snowball for Holyfield from then on. In the eleventh round, he exploded with nine punches -- two jabs, a chopping right to the head, two hooks, a right cross, a right uppercut, a left hook, and a final right hand -- that forced the referee to stop the fight.

What had been deemed impossible by most boxing fans happened: Evander once again proved that he was truly "The Real Deal".

3 James “Buster” Douglas KO10 Mike Tyson (February 10, 1990) / Fight Purse Disparity: $8.38 Million

James "Buster" Douglas's knockout win over "Iron Mike" Tyson is considered by many boxing pundits to be the biggest upset in heavyweight history and by some sports analysts to be the greatest sporting upset of all time. That was because Douglas was a talented but underachieving fighter whose previous attempt at a heavyweight belt had ended in a lopsided defeat to Tony Tucker. Meanwhile, Mike Tyson was, at that time, the undisputed heavyweight champion of the world, holding the WBC, WBA, and IBF titles simultaneously.

On the night of the bout, Buster dedicated the fight to his late mother and used his extra reach to hit the shorter champion. Mike, however, managed to drop Douglas in the eighth round. Nevertheless, James just came back stronger, snapping Tyson's head upward with a devastating uppercut in the tenth round and following it up with four punches to the head. That barrage caused Tyson to be knocked down for the first time in his career. In a famous scene, Mike fumbled for his mouthpiece, stuck one part in his mouth, and left the other end hanging out. He couldn't make it back to his feet in time.

Douglas, the 42-to-1 underdog, had become the undisputed heavyweight champion of the world.

2 Hasim Rahman KO5 Lennox Lewis (April 21, 2001) / Fight Purse Disparity: $11.18 Million

One problem with being an overwhelming favorite is the tendency to grow overconfident. Apparently, that's what happened to Lennox Lewis, the 15-to-1 favorite in his fight against the largely unheralded Hasim Rahman. Lewis would later admit that he was not 100% prepared for his fight against Rahman, who had been previously been knocked out by David Tua and Oleg Maskaev. The champion had been on the movie set for "Oceans Eleven". As a result, Lennox came to South Africa too late to properly acclimate to the unique conditions for the fight dubbed "Thunder in Africa".

Lewis's unpreparedness showed throughout the fight, especially in the fifth round when Rahman landed a monster right while Lewis was on the ropes. "The Lion" was floored, and with blank eyes, looked like he was lost in an African jungle. Fight over.

1 Bernard Hopkins TKO12 Félix Trinidad (September 29, 2001) / Fight Purse Disparity: $13.81 Million

A look at the names involved in the final of "The Middleweight World Championship Series" might make classifying it as an upset seem crazy. But Félix Trinidad really was overwhelmingly favored to unify all three titles (WBC, WBA, IBF)  to become the first undisputed middleweight champion since Marvin Hagler. After all, the Puerto Rican entered the unification fight as one of the best pound-for-pound fighters in the world, undefeated with forty straight wins. Meanwhile, his opponent Bernard Hopkins seemed to be, at 36 years of age, on the downside of his career.

While the first few rounds of the fight started slowly with both boxers feeling each other out, it was Hopkins who eventually found his rhythm and danced his way around Trinidad. As a result, before the last round, Félix was slumped in his corner having been exhausted as a result of the American's surprising approach to the match. In the twelfth, Bernard landed punch after punch, and midway through the round, connected with a huge right to the chin that left Trinidad crumpled on the canvas. The referee had no choice but to stop the fight, which Bernard was leading on all scorecards.

Hopkins had pulled off a great upset to become the undisputed middleweight champion of the world.

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