Boxing is one of the most unpredictable sports. While some fighters reach the pinnacle of success, others suffer crushing defeats or fail to live up to their potential. Whether due to lack of discipline, bad career choices, or shocking upsets, these 10 heavyweights experienced some of the greatest failures in boxing history.
1. Mike Tyson vs. Buster Douglas
- Full Name: Michael Gerard Tyson
- Born: June 30, 1966 (New York, USA)
- Height: 5’10” (178 cm)
- Reach: 71” (180 cm)
- Stance: Orthodox
- Record Before the Fight: 37-0 (33 KOs)
- Significant Titles: Undisputed Heavyweight Champion (WBC, WBA, IBF)
Mike Tyson was an unstoppable force in the late 1980s, known for his ferocious knockouts and aggressive style. At just 20 years old, he became the youngest heavyweight champion in history. By 1990, he was the undisputed heavyweight king, destroying opponents in brutal fashion. He seemed unbeatable—until he met Buster Douglas.
Tyson entered the fight overconfident and out of shape, underestimating his opponent. Douglas, motivated by the recent passing of his mother, fought the perfect fight, using his jab and superior movement to keep Tyson at bay. In the tenth round, Douglas landed a devastating uppercut, followed by a flurry of punches that sent Tyson crashing to the canvas. Unable to beat the count, Tyson suffered his first professional loss, marking one of the biggest upsets in sports history.
This defeat signaled the start of Tyson’s decline. He would later lose his titles, serve prison time, and struggle to regain his dominance. Boxing, much like gambling, is full of unpredictable twists—one moment you’re on top, and the next, everything changes. And if you’re looking for a place to test your luck, Stay Casino offers a huge selection of games, generous bonuses and crusino online casino, and convenient payment options, making it the perfect spot for an exciting gaming experience.
2. Riddick Bowe’s Career Mismanagement
- Full Name: Riddick Lamont Bowe
- Born: August 10, 1967 (Brooklyn, USA)
- Height: 6’5” (196 cm)
- Reach: 81” (206 cm)
- Stance: Orthodox
- Record: 43-1 (33 KOs)
- Significant Titles: Undisputed Heavyweight Champion (1992)
Riddick Bowe had all the tools to be an all-time great. He was a powerful, skilled, and intelligent fighter, with one of the best jabs in heavyweight history. In 1992, he defeated Evander Holyfield to become the undisputed heavyweight champion. However, poor decisions and a lack of discipline led to the premature decline of his career.
One of the biggest mistakes of Bowe’s career was refusing to fight Lennox Lewis. Instead of defending his WBC title, Bowe famously threw the belt into a trash can, avoiding a showdown with the dangerous Brit. Many saw this as an act of cowardice, damaging his legacy.
Bowe’s struggles with weight and motivation became evident as his career progressed. By the mid-1990s, he was no longer in peak condition and suffered unnecessary punishment in the ring. His fights with Andrew Golota ended in chaos, with Golota repeatedly hitting him below the belt. After those wars, Bowe’s career never fully recovered.
Despite an impressive record, Bowe is remembered as a fighter who never fully lived up to his potential.
3. Anthony Joshua vs. Andy Ruiz Jr.
- Full Name: Anthony Oluwafemi Olaseni Joshua
- Born: October 15, 1989 (Watford, England)
- Height: 6’6” (198 cm)
- Reach: 82” (208 cm)
- Stance: Orthodox
- Record Before the Fight: 22-0 (21 KOs)
- Significant Titles: WBA, WBO, IBF, IBO Heavyweight Champion
Anthony Joshua was seen as the future of heavyweight boxing. A dominant champion with an Olympic gold medal and an incredible physique, he was expected to rule the division for years. On June 1, 2019, he made his U.S. debut against Andy Ruiz Jr., a last-minute replacement opponent.
Most experts predicted an easy night for Joshua, but Ruiz had other plans. After knocking Joshua down four times, Ruiz secured a seventh-round TKO victory, shocking the world. Joshua appeared confused, out of sorts, and unable to recover after the first knockdown.
This loss was a major setback for Joshua’s career. Although he avenged the defeat in a rematch, his aura of invincibility was shattered, and he later suffered further defeats to Oleksandr Usyk.
4. Sonny Liston’s Mysterious Losses to Muhammad Ali
- Full Name: Charles L. “Sonny” Liston
- Born: c. 1932 (Arkansas, USA) – exact birth date unknown
- Died: December 30, 1970 (Las Vegas, USA)
- Height: 6’1” (185 cm)
- Reach: 84” (213 cm)
- Stance: Orthodox
- Record: 50-4 (39 KOs)
- Significant Titles: WBA, WBC Heavyweight Champion
Sonny Liston was one of the most feared heavyweights of all time, known for his incredible punching power and intimidating presence. After dominating Floyd Patterson to become the world champion, he seemed unstoppable. However, his two losses to Muhammad Ali remain among the most controversial in boxing history.
In their first fight in 1964, Liston, heavily favored, was beaten by Ali’s speed and footwork. Liston quit on his stool before the seventh round, citing a shoulder injury. Many speculated that he simply gave up, unable to handle Ali’s skill and confidence.
The rematch in 1965 was even more suspicious. Ali knocked Liston out in the first round with what appeared to be a light punch, now known as the “phantom punch.” Many believe the fight was fixed, as Liston had alleged ties to organized crime.
These losses destroyed Liston’s reputation, and he never regained his former status. His mysterious death in 1970 only added to the intrigue surrounding his downfall.
5. The Fall of James “Buster” Douglas After Tyson
- Full Name: James “Buster” Douglas
- Born: April 7, 1960 (Columbus, USA)
- Height: 6’4” (193 cm)
- Reach: 83” (211 cm)
- Stance: Orthodox
- Record: 38-6-1 (25 KOs)
- Significant Titles: Undisputed Heavyweight Champion (1990)
Buster Douglas pulled off the greatest upset in boxing history by knocking out Mike Tyson. However, instead of building on this success, he became one of the sport’s biggest one-hit wonders.
After defeating Tyson, Douglas lost motivation. He gained over 30 pounds and entered his first title defense against Evander Holyfield in poor shape. Holyfield easily knocked him out in the third round, ending Douglas’ short reign as champion.
Following this embarrassing loss, Douglas disappeared from the boxing scene for several years. He later made a comeback, but he was never the same fighter. His story is a classic example of how fleeting success can be in boxing.
6. Deontay Wilder vs. Tyson Fury II
- Full Name: Deontay Leshun Wilder
- Born: October 22, 1985 (Tuscaloosa, USA)
- Height: 6’7” (201 cm)
- Reach: 83” (211 cm)
- Stance: Orthodox
- Record Before the Fight: 42-0-1 (41 KOs)
- Significant Titles: WBC Heavyweight Champion (2015-2020)
Deontay Wilder was one of the most dangerous punchers in heavyweight history. With an incredible knockout percentage and a reputation for ending fights with a single punch, he was seen as nearly unstoppable. However, his technical skills were often questioned, as he relied heavily on his right hand.
His flaws were fully exposed in his rematch with Tyson Fury in 2020. After their controversial draw in 2018, Wilder was confident he would knock Fury out in the rematch. Instead, Fury dominated the fight from start to finish, bullying Wilder, pushing him backward, and landing powerful shots at will. Wilder was dropped twice and stopped in the seventh round after his corner threw in the towel.
After the fight, Wilder blamed his defeat on numerous excuses, including his heavy ring-walk costume, which he claimed weakened his legs. Though he had a much better performance in their trilogy fight, losing again to Fury in 2021, the rematch was the moment when his aura of invincibility was truly shattered.
7. David Price
- Full Name: David Price
- Born: July 6, 1983 (Liverpool, UK)
- Height: 6’8” (203 cm)
- Reach: 82” (208 cm)
- Stance: Orthodox
- Professional Record: 25-7 (20 KOs)
- Significant Titles: British and Commonwealth Heavyweight Champion
David Price was once considered the future of British heavyweight boxing. A 2008 Olympic bronze medalist, he had size, power, and an intimidating presence. Many expected him to be the next dominant force in the division, but his career quickly fell apart due to his weak chin and inability to recover from knockdowns.
His downfall began with back-to-back knockout losses to Tony Thompson in 2013. These defeats shattered his confidence, and he was never the same fighter again. Every time he stepped up in competition, he suffered another brutal loss, often in dramatic fashion.
Despite his physical attributes, Price lacked the defensive skills and mental toughness needed to compete at the highest level. He eventually retired in 2019, regarded as one of British boxing’s biggest disappointments.
8. Michael Moorer vs. George Foreman
- Full Name: Michael Lee Moorer
- Born: November 12, 1967 (Brooklyn, USA)
- Height: 6’2” (188 cm)
- Reach: 78” (198 cm)
- Stance: Southpaw
- Record Before the Fight: 35-0 (30 KOs)
- Significant Titles: WBA, IBF Heavyweight Champion (1994)
Michael Moorer made history as the first southpaw heavyweight champion, defeating Evander Holyfield to win the WBA and IBF titles in 1994. He was young, skilled, and technically sound. But his reign ended in one of the most shocking upsets in boxing history.
In his first title defense, Moorer faced 45-year-old George Foreman. Moorer dominated most of the fight, using his superior speed and boxing skills. However, he made a critical mistake—he stood directly in front of Foreman without moving his head. In the tenth round, Foreman landed a single powerful right hand that knocked Moorer out cold.
This fight made Foreman the oldest heavyweight champion in history and permanently damaged Moorer’s legacy. Despite later regaining a version of the heavyweight title, he was never regarded the same way again.
9. Shannon Briggs
- Full Name: Shannon Briggs
- Born: December 4, 1971 (Brooklyn, USA)
- Height: 6’4” (193 cm)
- Reach: 80” (203 cm)
- Stance: Orthodox
- Professional Record: 60-6-1 (53 KOs)
- Significant Titles: WBO Heavyweight Champion (1997)
Shannon Briggs had charisma, power, and a larger-than-life personality. He was known for his aggressive style and his relentless self-promotion, often calling out top fighters with his signature phrase: “Let’s go champ!” However, despite all the talk, Briggs’ career was filled with missed opportunities.
His biggest win came in 1997 when he controversially defeated a 48-year-old George Foreman for the WBO title. But he lost the belt in his very first defense against Lennox Lewis, getting brutally knocked out in five rounds.
Briggs continued fighting for years, chasing big paydays rather than serious competition. His resume lacked wins over prime elite opponents, and many saw him as more of a showman than a true contender.
10. Audley Harrison
- Full Name: Audley Harrison
- Born: October 26, 1971 (London, UK)
- Height: 6’5” (196 cm)
- Reach: 86” (218 cm)
- Stance: Southpaw
- Professional Record: 31-7 (23 KOs)
- Significant Titles: Olympic Gold Medalist (2000)
Audley Harrison entered the professional ranks with massive expectations after winning gold at the 2000 Sydney Olympics. He was touted as the future of British heavyweight boxing, but his career was a major disappointment.
Harrison’s biggest problem was his lack of aggression. He had the size and skills to be a top contender, but he often hesitated to throw punches. His most humiliating moment came in 2010 when he fought David Haye for the WBA heavyweight title. Harrison landed just one punch in three rounds before getting knocked out. After numerous failed comebacks, Harrison retired with a reputation as one of boxing’s biggest flops.