There’s a reason promoters stage fights featuring Goliaths vs. Davids. Usually there’s a ton of money involved. But also, strange things have been known to happen in the boxing ring. Like, for example, the 10 biggest upsets in boxing history, which you’ll find on the following pages.
Buster Douglas v. Mike Tyson (Tokyo, 1990)
Favorite: Iron Mike was at the top of his game in 1990. Only one book took odds on the fight, considered a warm-up for Tyson vs. cruiserweight champ Evander Holyfield, and Buster was a 42-1 shot.
What Actually Happened: Three weeks before the fight Douglas’ mother died, and ever since, athletes have been looking to bottle whatever that did to him. Douglas dominated Tyson from the word go and put him down for the first time in his career—and for the count—in the tenth round.
Aftermath: Douglas refused a rematch and lost his first title defense to Holyfield in the third round, retiring briefly thereafter. He later ballooned up to 400 pounds and went into a diabetic coma, then mounted a respectable comeback before retiring again at 38-6-1. Only in America.
Joe Louis v. Max Schmeling I (New York, 1936)
Favorite: Joe Louis was a hero of black America in the 1930s, the first successful black boxer from the north. Schmeling, a hero of Nazi Germany and former world champ, was considered little more than a stepping-stone for Louis on the way to the world title.
What Actually Happened: Schmeling knocked Louis down and out for the first time in his career.
Aftermath: Legendary black poet Langston Hughes reported seeing “grown men weep like children” on the streets of Harlem. But there was redemption: Louis took out Schmeling two years later as champ. By the way, Schmeling was no Nazi. He risked his life to save Jewish children in 1938.
George Foreman v. Michael Moorer (Las Vegas, 1994)
Favorite: Here’s a hint—he wasn’t 46 years old.
What Actually Happened: Moorer basically fought Foreman for the purse money and because it would be an easy win. Foreman wasn’t even ranked at the time of the fight. During the tenth round, however, Foreman landed a good short right to Moorer’s chin and it was over.
Aftermath: The WBA stripped Foreman of the belt for refusing to fight Tony Tucker, and the IBF stripped him of their strap for refusing a rematch with Axel Schulz. He dropped the Lineal World Heavyweight Title to Shannon Briggs in Vegas, then retired to become a novelty grill salesman and hang out with a million kids named George.
Michael Spinks v. Larry Holmes (Las Vegas, 1986)
Favorite: This battle was Spinks’ first fight as a heavyweight. Holmes is regarded to this day as having one of the best left jabs in the history of boxing. A light heavyweight had never won a heavyweight title before, until…
What Actually Happened: A unanimous decision and a whole lot of controversy. Holmes would have tied Rocky Marciano’s winning streak had he defeated Spinks. Instead, judges ruled against him and he urged them to “kiss my big black behind” before stating that “Rocky Marciano isn’t fit to carry my jock strap.”
Aftermath: Holmes retired, before going through the requisite “comebacks.” Spinks dropped the title to Tyson in his first and only professional defeat. The Ring magazine dubbed this fight its “Upset of the Year.”
Muhammad Ali v. George Foreman (Kinshasa, Zaire, 1974)
Favorite: It’s hard to imagine Ali being the underdog, but everyone’s money was on Foreman. At 32 Ali was considered past his prime and easy pickings for the powerful and ascendant Foreman.
What Actually Happened: If you sat through the abomination called Rocky Balboa you know that being able to hit is only part of the sweet science. The other part is being able to get knocked in the face repeatedly without going down. Most of Ali’s training involved learning to take punishment and wear his opponent down in the clinch. Foreman was worn way down by the end of the fifth, earning classic Ali taunts like, “They told me you could hit,” and, “Is that all you got, George?” After the latter, Foreman later reported thinking, Yep… that’s about it.
Evander Holyfield v. Mike Tyson (Las Vegas, 1996)
Favorite: People thought Tyson was literally going to kill Holyfield in the ring.
What Actually Happened: This was closer to a blood feud than a boxing match. Holyfield kept catching Tyson with his head and there is still controversy as to whether or not it was intentional. In the third round, Tyson had had enough of Holyfield’s shit and decided to put some of what he learned in the joint to work by biting part of Holyfield’s ear off before spitting it on the ground. Tyson claimed a punch injured Holyfield’s ear, to which referee and all-around badass Mills Lane responded, “Bullshit.” Lane disqualified Tyson for biting a second time.
Aftermath: Tyson was suspended by the WBA and had his boxing license pulled in Nevada, effectively ending his career. He went on to become the street philosopher we all know and love, eventually apologizing to Holyfield on Oprah. How’s that for some bromance?
James J. Corbett v. John L. Sullivan (New Orleans, 1892)
Favorite: John L. Sullivan was a legend in his own time and representative of the monstrous style of pugilism that typified early boxing, even under Queensbury Rules.
What Actually Happened: Unfortunately for Sullivan, the time of the brawler who rushed in with a series of big rights was over. James J. Corbett is known as “The Father of Modern Boxing” precisely because his more scientific style was able to quickly dispatch a brawler like Sullivan. Corbett didn’t land a punch until the third round, using feints, footwork and jabs to turn the soon-to-be-former champ into a sweaty mess before dropping him in the 21st. (Fights went longer then.)
Aftermath: Modern boxing.
Muhammad Ali v. Sonny Liston (Lewiston, Maine, 1965)
Favorite: Sonny Liston was largely regarded as the toughest man in the world and perhaps the biggest badass to ever enter the ring. He was itching for a rematch after an unsatisfying loss to Ali a year earlier.
What Actually Happened: In one of the most controversial episodes in modern boxing, Liston may or may not have been hit before he hit the canvas. Ali stood over him shouting, “Get up and fight, sucka!” But Liston remained on the ground. Many speculated Liston bet against himself and took a dive to pay off Mafia debts or out of fear of retaliation from the Nation of Islam.
Aftermath: Ali went on to fight Ernie Terrell, a man who was either incredibly stupid or incredibly masochistic and insisted on calling Ali “Cassius Clay,” to regain his WBA title. Sports Illustrated’s Tex Maule called it “a wonderful demonstration of boxing skill and a barbarous display of cruelty,” as Ali carried Terrell for 15 rounds taunting, “What’s my name, Uncle Tom?” Ali was later stripped of both belts for refusing to register for the draft.
Marvin Hagler v. Sugar Ray Leonard (Las Vegas, 1987)
Favorite: Hagler went over ten years without a defeat and had held the title for seven when he squared off against the twice-retired Leonard, who had battled a coke addiction and a serious eye injury.
What Actually Happened: Leonard won, albeit by a decision that’s controversial to this day.
Aftermath: Leonard spent much of the next couple years ducking a rematch with Hagler, before retiring again and making another comeback bout against Hector Camacho. He lost, but he also became the first member of the International Boxing Hall of Fame to fight after induction.
Manny Pacquiao v. Oscar De La Hoya (Las Vegas, 2008)
Favorite: De La Hoya was the heavy favorite, this being the time before the mythos surrounding Pacquiao had been built. Only once had Pac fought above 130.
What Actually Happened: De La Hoya’s corner threw in the towel after the eighth, but it was painfully obvious about a minute into the fight that De La Hoya was toast. For what it’s worth, De La Hoya’s last loss before the Pacquiao fight was against Floyd Mayweather.
Aftermath: The Golden Boy retired. Pac fought some tomato cans, ran for Filipino Congress and refused to submit to American anti-doping standards in a fight against Floyd Mayweather. We’re still not totally sure who’s ducking whom, but if Mayweather wins this weekend, they’d better freakin’ fight.