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The Biggest Upsets in Boxing

Rocky Balboa, Sylvester Stallone, Carl Weathers

A look at some of most surprising losses in boxing history.

Throughout history, upsets have occurred in every sport. Boxing is no exception. People tend to follow their favorite athletes and may not consider other factors that can determine an outcome of a match, such as age, skill level or desire. In addition, oddsmakers can have considerable influence on people’s opinion on the outcome of a sporting event.


• Gene Tunney dominated Jack Dempsey in front of a crowd of 120,000.
• Holmes was one victory away from tying Rocky Marciano’s 49-0 record.
• Mike Tyson lost his match to Douglas before he ever stepped in the ring.

Bookies, gambling houses and online sportsbooks in the US mostly look at the statistical records of an athlete or team to determine the odds. Often personal problems or level of interest in boxers are overlooked completely. We will see examples of fights that were considered upsets, but may not have been that surprising, if looked at more closely. Of course factors determining sports outcomes are normally easier in retrospect.

Four upsets from the past

Schmeling Joe Louis KO
In 1926, Jack Dempsey was king of the world. Not only had he fulfilled all hopes of “great white hope”, but had been elevated to folk status. His charisma and machismo convinced all of his “invincibility.” That is except light heavyweight champ Gene Tunney who, in front of a crowd of 120,000 dominated Dempsey. Although the hopes and dreams of the masses were shattered, nobody questioned the judges.

Joe Louis was a god in 1936. Considered unbeatable, he was the first African American sports hero accepted by most Americans. The possibility for German boxer Max Schmeling was little. Schmeling studied Louis and discovered a weakness. In the fight, Louis’ habit of dropping his left hand before throwing a jab cost him to get outpointed in every round. Shocking the World, America found a new enemy in Schmeling.

In 1964, Cassius Clay let a psychological assault on the masses as well as his upcoming opponent Sonny Liston. Nobody gave a Clay defeat a second thought, until Clay spoke to every media outlet he could about his intention to bet Liston. Most people watched that fight just to see the 1960 Olympic gold medalist proven wrong. Liston couldn’t keep up with Clay and he won the heavyweight championship and Muhammad Ali was born.

In 1974, George Foreman was the most feared fighter on the planet Earth. He had knocked George Frazier and Ken Norton out after they had inflicted their damage on Ali. Zaire appealed to Ali and depressed Foreman, who trained little and stayed in his room. A cut during training forced Foreman to remain seven more weeks in the jungle. Statistically, this fight was Foreman’s to lose. Which according to US gambling news, he did ended up doing.

Four more recent upsets plus one for the ages

Douglas KOs Tyson
Anyone in their right mind, with any knowledge of boxing history, would think it crazy to bet against Roberto Duran. Well in 1983, Duran lost two of his last three bouts and considered washed up. Davey Moore, junior middleweight champ, was younger, won three title defenses and was fighting at home in Madison Square Garden. A root canal, days before the fight, plus eight rounds of torture by Duran equaled an upset.

In 1985, undefeated Larry Holmes took on Michael Spinks. Holmes, who was one victory away from tying Rocky Marciano’s 49 win, no loss record, was considered the favorite. A funny thing happened before the fight. In training, Holmes inflicted damage to his thumb. With such a record on the line, one might think Holmes would postpone the fight until his thumb heals. He refused and Spinks technically crafted a victory.

In 2004, Roy Jones Jr. was considered one of the best pound-for-pound fighters ever. The man had quickness, style and the skill to put it all together. Facing Antonio Tarver, Jones was able to win by decision. A rematch six months later seemed customary and unpredictable. When the fight began, Jones was impressive outperforming Tarver. That would end with a left hood from Tarver that made his victory obvious and counting futile.

In 2008, Oscar De La Hoya was prominent and knew what he wanted. In an effort to fight Floyd Mayweather he signed up to take on Manny Pacquiao. Considering Pacquiao was lighter and never fought while over 130 pounds, most people waging along US gambling laws gave the advantage to De La Hoya. Pacquiao was ready and lead in every round of the fight as well as leading De La Hoya to retirement after the bout.

Mike Tyson lost by knockout in 1990. It still doesn’t sound right even though it’s a historical fact. Despite being burdened by his personal life, James “Buster” Douglass was never taken seriously for a moment. Tyson took neither himself nor Douglass seriously during that time. Only one casino in Vegas would take bets at 42-1 odds. Despite this, Douglass dominated the fight and survived a late count in the 10th round.

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