Biggest Boxing Upsets Based on Betting Odds

In every boxing fight, there is a favorite and an underdog. Whether this is determined by analysis or betting odds, fans have a general idea of who is going to win the fight.

The favorite is the fighter than is expected to win the fight. He is perceived to have an advantage over his opponents and is the one who has a better path to success. However, things don’t always go as planned in a sport where one punch can change destiny.

When the underdog emerges victorious, it is called an upset. The sport of boxing is rich in upsets with tales of fighters written off coming off with epic performances to beat the odds and capture glory.

Here are the biggest upsets in boxing history based on betting odds:

1. Buster Douglas vs Mike Tyson 1990

Mike Tyson entered his fight against James “Buster” Douglas as a -4200 favorite. Iron Mike was unbeaten in 37 fights and had butchered every opponent he has faced to become undisputed heavyweight champion. Tyson didn’t just drop everybody, he produced highlight-reel knockouts that made him look unstoppable during his prime.

Douglas was at best a mediocre challenger with four losses. Tyson had beaten much better opposition previously and Douglas looked like a footnote in Iron Mike’s Japan vacation. However, Buster had other plans. He boxed evenly with Tyson for nine straight rounds before landing a killer uppercut in the 10th that started Tyson’s downfall. A sharp combination later in the round dropped Iron Mike who was unable to beat the count.

2. Evander Holyfield vs Mike Tyson, 1996

Six years after suffering the biggest upset loss in heavyweight boxing history, Iron Mike Tyson fell prey to another giant-killer in Evander Holyfield. Holyfield had gone 2-2 in his last four bouts and had just suffered his first knockout loss to Riddick Bowe one year earlier.

On the other hand, Mike Tyson was a -2500 favorite after he had beaten his first four opponents during his comeback. Iron Mike had not fought in the previous four years while serving a prison sentence for a rape conviction. Upon his release, he resumed his boxing career and annihilated his first four opponents during his comeback trail. But Holyfield shocked the world by deciding to slug it out with Tyson. He would outpunch Iron Mike before the fight was stopped in the 11th round.

3. Anthony Joshua vs Andy Ruiz Jr., 2019

California’s Andy Ruiz shocked the world last year when he came to the Madison Square Garden and dealt British champion, Anthony Joshua, his first career loss. Ruiz entered his second title challenge on a month’s notice after Joshua’s original opponent, Jarrell Miller, was disqualified for failing a drug test.

Ruiz came back after suffering his first career knockdown in round three to dominate Joshua in the next four rounds. The challenger would drop the champion four times during the fight. In the 7th round, Joshua looked nothing like the -2400 favorite he was entering the fight. Joshua looked unbeatable before that fight but he left New York wondering if he will recover from the loss.

4. Corrie Sanders vs Wladimir Klitschko

Wladimir Klitschko was a -2000 favorite during his WBO title defense against South Africa’s Corrie Sanders in 2003. Klitschko had won 16 straight fights including five straight successful defenses of the WBO title, all of which were knockouts. On the other hand, Sanders was 39-2 but had never fought a notable opponent aside from former champions Hasim Rahman and Bobby Czzyz, who were both in their twilights when he fought them.

But Sanders had fast-hands and powerful punches. He was able to slip Klitschko’s long jabs and land his big punches on the champion. Sanders would launch a hellacious attack that would drop Klitschko four times in two rounds. The shocking win earned him Upset of the Year honors. He would go on to challenge Klitschko’s brother Vitali but would lose that match.

5. Lennox Lewis vs Hasim Rahman

Nobody thought that Hasim Rahman would beat Lennox Lewis when these two heavyweights first fought in 2001. Two years earlier, Lewis established himself as the best heavyweight of the generation when he defeated Evander Holyfield convincingly. Then Rahman also had a plodding style that looked tailor-made for Lewis to look good against.

The -2000 favorite Lewis fought as expected in the first four rounds of the bout He kept his opponents at bay with his long jabs and landed his big right hand almost at will. Rahman missed punch after punch but did not get frustrated. In the 5th, Lewis smiled at Rahman while backpedaling after dodging a series of blows by the challenger. Out of nowhere, Rahman connected a huge overhand right that sent Lewis down for good.

6. James Braddock vs Max Baer

James Braddock upset Max Baer in the biggest heavyweight upset in 50 years. The champion Baer entered the bout as a -1000 favorite against his challenger. But Braddock would outbox Baer in 15 rounds to earn the title of Cinderella Man. The event was later turned to a movie that featured Australian superstar Russell Crowe.

Baer was a massive puncher who had just won the heavyweight champion by rag-dolling the giant Primo Carnera for 11 rounds before the fight was mercifully stopped. Meanwhile, Braddock had lost 25 fights and wasn’t considered a serious threat to the new champion. However, Braddock turned in one of the biggest boxing upsets ever.

7. George Foreman vs Muhammad Ali

George Foreman was a -700 favorite when he fought Muhammad Ali in the famous Rumble in the Jungle in Zaire on October 30, 1974. Foreman was on a tear in the heavyweight division after winning Olympic gold in 1968. He had destroyed Ali’s rival Joe Frazier in two rounds and disposed of Ken Norton very easily in two rounds as well.

But Ali solidified his status as the greatest of all-time as he employed his rope-a-dope strategy on the champion. Foreman threw the entire arsenal at Ali but could not land his big blows. The challenger countered Foreman all night long and earned a stoppage win in the 8th round.