Biggest Upsets in Boxing History: Top 10 Shocks Ranked by the Odds

Tokyo Dome, February 11, 1990. Tyson walked in as the undefeated, undisputed champion, holding the WBC, WBA and IBF belts, fresh off a 93-second knockout of Carl Williams. Douglas was ranked No. 7 by The Ring and had lost to Tony Tucker by 10th-round stoppage in 1987. Some books had the line at 35-1. The famous number, 42-1, is the one that stuck.

Douglas boxed the fight of his life for nine rounds, then survived the moment that nearly erased all of it. In the final ten seconds of the eighth, Tyson landed a right uppercut that put Douglas down. He got up as referee Octavio Meyran reached nine, and the bell saved him. Don King screamed about a long count for days.

In the tenth, Douglas landed an uppercut, followed with four more punches, and Tyson was counted out on his knees, fumbling for his mouthpiece. The WBA and WBC briefly suspended recognition of Douglas as champion. Four days later the protest collapsed and the result stood. It is still the measuring stick for every upset in every sport.

Madison Square Garden, June 1, 2019. Joshua was 22-0 with 21 knockouts and making his American debut with the WBA, IBF, WBO and IBO belts. Ruiz was not even the planned opponent. Jarrell Miller failed three VADA tests, New York denied him a license, and Ruiz put his name forward. Terms were agreed within a week and the fight was confirmed on May 1.

Ruiz, 32-1, opened at 25-1 and was still around 13-1 at the opening bell. Joshua dropped him in the third and looked ready to close the show. Instead Ruiz got up and put Joshua down twice before the round ended. Two more knockdowns came in the seventh, at 2:27 and 1:59 remaining, and referee Michael Griffin waved it off.

Two judges actually had Ruiz ahead 57-56 at the stoppage. Joshua reportedly earned around $25 million and Ruiz about $7 million. Joshua won the rematch later that year, but the first fight is the one that follows him.

Carnival City, South Africa, April 22, 2001. Lewis was the recognized heavyweight champion of the world and treated the trip like a routine defense. Rahman was quoted anywhere from 16-1 to 20-1. He landed one straight right hand in the fifth round and Lewis went down flat.

The rematch tells you how big the upset was. On November 17, 2001 at Mandalay Bay, Lewis knocked Rahman out in the fourth round and took back the WBC, IBF and IBO titles. Rahman was paid $10 million for that night and Lewis $11 million, which means a 20-1 shot turned one punch into the biggest payday of his life twice.

Earls Court, London, July 10, 1951. Robinson had taken the middleweight title from Jake LaMotta five months earlier and was touring Europe, fighting eight non-title bouts along the way. London paid him $84,000, a record for a fighter in a British ring. Turpin, a 20-1 longshot in Fight City's accounting, outboxed him for 15 rounds and took the title on points, ending a run of around 90 fights without a loss.

Robinson got it back a few months later with a 10th-round stoppage. Turpin never reached that height again, but one night in London he beat the man most people still call the best pound-for-pound fighter who ever lived.

Miami Beach, February 25, 1964. Liston was the most feared heavyweight on earth and Clay was a loud young contender most writers expected to get hurt. The line was 7-1 or 8-1 depending on the source. Clay outboxed Liston for six rounds, and Liston stayed on his stool before the seventh.

The rematch in Lewiston, Maine on May 25, 1965 ended in the first round and produced the most famous boxing photo ever taken. The first fight is where the Ali era actually started.

Las Vegas, November 9, 1996. Holyfield was widely written off as a faded former champion, and the books opened him at 25-1. Enough smart money came in that the line closed near 5-1, which is why this one sits below the longer shots even though it felt just as impossible in the room.

Holyfield fought Tyson the way nobody had since Douglas: head-on, with a longer jab and a shoulder in the chest. Tyson got battered along the ropes late until referee Mitch Halpern stopped it in the eleventh. The rematch on June 28, 1997 ended with Tyson disqualified for biting Holyfield's ears.

Yankee Stadium, June 19, 1936. Louis was 27-0 and being lined up for a title shot. Schmeling, a 10-1 underdog, studied film, found that Louis dropped his left hand after jabbing, and spent twelve rounds timing a right hand over the top. Louis was knocked out in the twelfth.

The rematch on June 22, 1938, again at Yankee Stadium in front of more than 70,000, lasted two minutes and four seconds. Louis dropped Schmeling three times. The first fight remains the biggest upset of Louis's career and the only loss in his prime.

Las Vegas, February 15, 1978. Spinks had only seven professional fights. Ali treated it like a tune-up. The line opened at 10-1 and closed around 8-1. Spinks threw punches for fifteen rounds and took a split decision and the heavyweight title.

Ali fixed it seven months later. On September 15, 1978 at the Superdome in New Orleans, in front of roughly 63,350 people, he won a unanimous decision by scores of 10-4, 11-4 and 10-4 and became the first three-time heavyweight champion.

Madison Square Garden Bowl, Queens, June 13, 1935. Braddock had broken his hands, worked the docks as a longshoreman and taken public relief to feed his family. Baer was the champion, a huge puncher, and a 10-1 favorite. Braddock boxed carefully for fifteen rounds and won a unanimous decision. The Cinderella Man story is one of the few in boxing that needed no exaggeration.

Caesars, Atlantic City, September 27, 1986. Curry was 25-0, the undisputed welterweight champion and, for many, the best fighter in the world. Honeyghan was a brash Londoner the American press barely knew. He walked Curry down for six rounds, opened a cut over the left eye, and the ringside doctor advised Curry's corner to stop it after the sixth.

None of the accounts I read put a firm betting line on it, only that Honeyghan was a massive underdog, so it anchors the list rather than leading it. In terms of taking apart a reputation in one night, it is right there with Douglas and Ruiz.