The world of boxing has seen its fair share of formidable titans, and among these giants, Mike Tyson, also known as “Iron Mike” or “The Baddest Man on the Planet,” stands out as one of the most iconic figures. Tyson’s prime years were filled with tales of his awe-inspiring victories and the fear he instilled in his opponents. Yet, even the greatest have their moments of downfall. Tyson was not invincible.
Mike Tyson lost 6 over 58 fights in his professional boxing career. His losses were to James “Buster” Douglas, Evander Holyfield (twice), Lennox Lewis, Danny Williams, and Kevin McBride, marking poignant chapters in Tyson’s illustrious career.
So, strap in as we take a walk through memory lane, revisiting the unexpected turns in Tyson’s illustrious career. Whether you’re a lifelong fan of Tyson or simply a boxing enthusiast curious about the sport’s history, this compilation of Tyson’s losses offers a fascinating insight into the career of one of the greatest fighters in boxing history.
1. Buster Douglas
On the morning of February 11, 1990, an undefeated Mike Tyson, the reigning heavyweight champion, faced off against Buster Douglas. Ten demanding rounds later, Tyson was left stunned on the canvas.
Before the match, Douglas was seen as a longshot, with Vegas’s Mirage casino placing him as a 42-1 underdog. Tyson himself didn’t take Douglas seriously, regarding him as an easy obstacle. Tyson admits he didn’t bother reviewing Douglas’s previous fights or adequately prepare for this match, unaware of the stunning upset in store.
Yet, on the day of the match, Tyson was clearly ill-prepared, emotionally unstable, and reportedly distracted by his notorious exploits in Tokyo. On the other hand, Douglas, dealing with personal tragedy – the loss of his mother, separation from his wife, and his child’s mother being diagnosed with terminal cancer – had arrived in Tokyo with a resolve to fight. And fight he did, with incredible resilience.
On the day of the fight, Tyson’s performance was lackluster, a sharp contrast to his usual ferocity. Initial rounds might have fooled spectators into thinking Tyson was just off to a slow start, with Douglas only landing minor blows. However, Tyson’s shaky knees in the second round, after a powerful right hook from Douglas, hinted at a momentum shift.
By rounds four and five, Douglas took the lead, with Tyson’s eye starting to swell. It wasn’t until round seven that Tyson momentarily regained his footing, landing a series of blows. But Douglas wasn’t daunted, avoiding Tyson’s attacks and retaliating with two powerful punches that sent Tyson reeling.
Tyson managed to floor Douglas with a right uppercut, and many thought this signaled a comeback. But Douglas kept pressing on in the ninth round, driving Tyson back to the ropes. By the tenth round, the inconceivable had happened – Tyson was defeated, and James ‘Buster’ Douglas was declared the new heavyweight champion amid the ensuing confusion.
Douglas had demonstrated remarkable determination, while Tyson, plagued by reports of an unruly lifestyle and insufficient training, had come in woefully underprepared. His cornermen were ill-equipped to handle the crisis.
Years later, Douglas revealed that he believed Tyson would falter if he continued to attack since he had nothing to lose. Tyson did ultimately succumb. Douglas’s relentless jab and potent right repeatedly hit their mark, even as he himself took damage.
Tyson was defeated, an outcome that was unthinkable up until that moment. The underdog emerged victorious, and Buster Douglas deserves recognition for overthrowing the seemingly invincible Tyson in one of boxing history’s most unexpected upsets.
2. Evander Holyfield
In the wake of Mike Tyson’s return to the boxing ring following his imprisonment in March 1995, he reasserted his dominance with a string of victories. His return, though short-lived, reignited his reputation as the world’s leading heavyweight.
When the upcoming match against Evander Holyfield was announced, critics voiced concerns for Holyfield’s well-being, as he was widely considered an underdog. Given his recent lackluster performance, many believed Holyfield’s prime years were behind him and that he was no match for Tyson.
Prior to the fight, the Nevada State Athletic Commission mandated a comprehensive medical examination for Holyfield. Tyson’s anticipated quick knockout was the talk of the town.
In a sold-out MGM Grand, the match began with Tyson landing the first punch, leading many to believe that the prediction might come true. However, the match took an unanticipated turn as Holyfield retaliated, parrying Tyson’s strikes with sharp left hooks and powerful right hands.
In an unexpected turn of events, Holyfield trapped Tyson against the ropes, landing direct hits, including a mighty left punch that clearly stunned Tyson. Continuing his surprise assault, Holyfield used his height, reach, and power to his advantage and delivered a series of calculated headbutts.
Tyson seemed lost against an opponent who refused to play the anticipated role of the overwhelmed challenger. In contrast, Holyfield grew increasingly assertive, forcing Tyson on the defensive and landing powerful, clean punches.
Tyson’s reputation had set the stage for an epic confrontation akin to Ali vs. Frazier. Holyfield’s unanticipated resilience against Tyson created an electrifying spectacle. Tyson managed to claim the fifth round with a powerful left hook-left uppercut combination, but the match’s pattern had been set: Holyfield was dictating the pace, overpowering Tyson, and swiftly countering his assaults.
During the sixth round, Holyfield landed a powerful right punch, causing a cut on Tyson and scoring a knockdown. As the fight progressed, Tyson’s once-intimidating persona began to fade, revealing a stark lack of self-confidence.
The tenth round marked Tyson’s downfall. Holyfield landed a right hook to Tyson’s temple, making his legs buckle. Instead of clinching, Tyson continued to exchange punches and was met with another punishing right hand, pushing him backward.
Despite being visibly injured, Tyson entered the eleventh round, only to be swiftly defeated by Holyfield. Tyson was left defenseless against the ropes, prompting the referee to call the fight off.
Like Buster Douglas before him, Holyfield faced Tyson’s intimidation head-on and stood his ground. The match exposed Tyson as a one-dimensional boxer who heavily relied on his brute force and his opponents’ fear. On the other hand, Holyfield, who was largely dismissed by critics, proved that he still possessed the skill and willpower to compete at the highest level, thus dismantling the myth of Tyson’s invincibility.
3. Evander Holyfield 2nd fight
One of the most memorable sports events of the 90s was the rematch between Evander Holyfield and Mike Tyson. Following Holyfield’s surprising victory over Tyson a year prior, the two fighters squared off again. This rematch, while only lasting three rounds, would be remembered for its shocking events.
The fight started where their previous encounter had left off, with Holyfield in command, effectively repelling Tyson’s aggressive tactics. By the conclusion of the initial round, Holyfield had successfully inflicted damage on Tyson. He displayed his superior technical skills and physicality, effectively using headbutts, shoulder checks, and forearm strikes to keep Tyson at bay.
The second round saw Tyson sustain a cut above his right eye due to an “accidental headbutt,” marking the second such incident in their two fights. Tyson’s visible frustration led him to frequently look towards referee Mills Lane, seemingly in hope of intervention. Lane, however, attributed the headbutt to an accident and allowed Holyfield to proceed with his aggressive tactics.
Tyson, who appeared to be on the back foot, surprisingly burst forward with aggression in the third round, landing powerful left hooks and right punches. However, Holyfield remained unfazed, maintaining control and rendering Tyson’s temporary rally ineffective.
In a shocking turn of events, Tyson bit off a chunk of Holyfield’s right ear during a clinch, causing Holyfield visible distress. This act marked a complete loss of control for Tyson. After consulting with the ringside doctor and the state athletic commissioner, referee Lane permitted the fight to continue but deducted two points from Tyson.
Tyson’s anger didn’t subside, leading him to bite Holyfield’s left ear as well, an act that resulted in his disqualification. Following his disqualification, Tyson tried to attack Holyfield again, causing chaos in the ring. Several security personnel struggled to restrain Tyson, leading to a surprising and chaotic scene.
The loss marked the end of Tyson’s post-prison career phase when he had re-established his reputation as “The Baddest Man on the Planet” and was considered one of the top heavyweights. His allure was no longer based on his boxing skills but on the unpredictability of his rage-driven antics. Spectators remained glued to the Mike Tyson saga, wondering what new lows his anger might lead him to.
4. Lennox Lewis
In 1983, even before Lewis made his first appearance in the Olympic Games Tyson failed to qualify, the two had a heated sparring session. Lennox Lewis later shared a prediction made by Tyson’s coach, Cus D’Amato, that they would eventually face each other in a professional bout.
By 1988, Lewis had won a gold medal at the Olympics, while Tyson had already secured the undisputed heavyweight champion title. A fight between Lewis and Tyson seemed improbable, primarily due to their divergent professional paths.
By 1992, Lewis had ascended the professional ladder, but he was still considered ill-equipped to face Tyson. However, the prospect of such a fight was delayed as Tyson was serving a prison term for a rape conviction. Tyson returned to boxing in 1995, reclaimed the WBC and WBA belts, and even paid Lewis a “step aside” fee to face Bruce Seldon in 1996.
After his controversial loss to Holyfield, where Tyson bit Holyfield’s ears, he faced an 18-month ban from the Nevada State Athletic Commission. Meanwhile, Lewis was making his mark as a leading heavyweight.
At last, the stage was set for the much-anticipated Lewis-Tyson bout at The Pyramid in Memphis, Tennessee. An unusual scene greeted attendees as security guards split the ring to prevent any pre-fight chaos.
The fight went as expected: Tyson charged forward with power punches, Lewis maintained distance and employed his jab. Lewis staggered Tyson with an uppercut in the first round and cut Tyson’s right eye in the third round with sharp jabs. Despite Lewis’s dominance, Tyson managed to land a successful left hook.
In the fourth round, Tyson was hit with a powerful right hand and was partially pushed down, leading referee Eddie Cotton to deduct a point from Lewis for pushing. Despite Lewis’ dominance, his trainer, Emanuel Steward, warned him to finish off Tyson before an unexpected punch could alter the course of the fight.
In the fifth round, Lewis cut Tyson over the left eye. Tyson’s attempts to retaliate were mostly ineffective, managing only to slightly swell Lewis’ left eye in the sixth round with a singular powerful punch. By the seventh round, the match was one-sided, with Tyson showing incredible tenacity to continue into the eighth round.
The eighth round witnessed Tyson’s feeble resistance being suppressed by Lewis’s dominant uppercuts, leading to a knockdown. A powerful right-hand punch from Lewis ended the fight, leaving Tyson flat on the canvas. The anticipated face-off, which had been foreseen years ago by D’Amato, had finally taken place, with Lennox Lewis emerging as the undisputed winner.
5. Danny Williams
The professional boxing match between Mike Tyson and Danny Williams on July 30, 2004, was an unexpected showdown. Billed as ‘Return for Revenge,’ Tyson, a former heavyweight champion, entered the bout as a 9-to-1 favorite with bookmakers.
Yet, the underdog Williams, with unwavering confidence, triumphed by knockout at 2:51 of the fourth round. This fight marked Tyson’s second to last ring appearance.
Initially, Tyson displayed his superior fighting skills, rattling Williams with a powerful left uppercut in the first round’s midsection. Williams seemed to be at the receiving end but held on to Tyson, making it through the round without any knockdowns, even after Tyson landed two additional major hits.
However, Tyson suffered a ligament tear in his left knee, which negatively affected his movement and punch-throwing ability throughout the match.
Williams seized this opportunity and landed powerful punches in the second round. Tyson managed to clinch the round on all three judges’ scorecards, yet his grip on the fight was evidently slipping. The third round saw Williams trying to keep up, despite losing two points for a late punch and a low blow. Tyson appeared exhausted in the fourth round, throwing and landing fewer punches.
With less than half a minute left in the fourth round, Williams launched a brutal combination, causing Tyson to hit the mat. Tyson made a delayed attempt to get up at the referee’s seven-count but failed to beat the ten-count, leading to Williams being declared the winner by knockout.
Tyson’s defeat had multiple contributing factors. His age, at 38 years old, and increased weight – tipping the scales at 233 pounds – played significant roles. A 17-month break from boxing and the knee injury suffered early in the fight significantly impacted his performance.
These weren’t just excuses; Tyson underwent surgery for a complex lateral meniscus tear by Dr. Richard Emerson, a well-known orthopedic surgeon. Emerson was amazed that Tyson was even able to box after the injury and walk unassisted out of the ring.
After the match, boxing promoter Bob Arum suggested that Tyson should have fought against less skilled opponents for his first few bouts following the hiatus. Tyson reportedly took the fight due to debts exceeding $30 million.
6. Kevin McBride
Mike Tyson’s last professional bout is a reminder of the inevitable passage of time and the decline even the greatest athletes face. Tyson, once feared as “The Baddest Man on the Planet,” went up against the relatively unknown Irish heavyweight Kevin McBride on June 11, 2005.
For McBride, it was an opportunity of a lifetime, the highlight of his career. Tyson, struggling with bankruptcy, fought mainly for financial benefits.
Tyson’s downfall became evident as the fight unfolded. At 38, Tyson was no longer the formidable powerhouse that his opponents feared. He stood 5’10” and weighed 233 pounds, substantially smaller than the 6’6″, 271-pound McBride. Tyson also seemed mentally unsettled. Known for his aggressive assaults, he seemed unusually restrained, allowing McBride to take the initiative and limit his movements.
Occasional punches from Tyson reminded his fans of his heyday, but these moments were fleeting. Despite a sudden surge of aggression in Round 4, his failure to knock McBride out was a clear sign of his waning abilities. McBride stood tall, absorbing Tyson’s onslaught and emerging unscathed.
By Round 6, Tyson’s desperation was evident. He resorted to illegal tactics such as attempting to break McBride’s arm and headbutting him, resulting in a two-point deduction. The once fearsome Tyson had exhausted all strategies, both legitimate and illegitimate. As the round ended, Tyson slumped to the canvas, his journey reaching a bitter conclusion.
Refusing to rise for the next round, a defeated Tyson made a melancholic sight in his corner. His loss led to a surprise win for McBride, but Tyson’s retirement announcement overshadowed it. Even with his financial issues, he had lost his fighting spirit.
Throughout the match, Tyson maintained his iconic appearance: a muscular, solid physique at age 38, still looking formidable. However, his performance was a sharp contrast to the fearsome warrior he once was. McBride easily countered Tyson’s initial defensive maneuvers.
As Tyson started showing signs of fatigue, McBride took control, pinned Tyson against the ropes, and landed solid uppercuts. This back-and-forth battle, while lacking technical prowess, provided an engaging spectacle.
In his last appearance as a professional boxer, Tyson apologized to the sport he loved and his loyal fans. He expressed regret for his lackluster performance and a desire to move forward in life. McBride enjoyed his momentary glory, but his career soon fizzled out, losing six of his next eight fights before retiring in 2011.
The end of Tyson’s career and McBride’s subsequent trajectory signaled the end of an era, reminding fans of the ruthless toll time takes on even the most impressive athletes.