When you’ve been labeled one of the greatest of all time, it means your portfolio is stacked with incredible feats. In boxing, no conversation about the best of the best without including Mike Tyson. The indomitable champion remains one of the most ruthless fighters in the ring. While he’s long since stayed out of the ropes, Mike Tyson is set to make a return against Jake Paul this July.
Tyson’s career is marked by several highs and lows: from his meteoric rise to becoming the youngest heavyweight champion in history to serving time in prison and making a killer comeback. However, in the ring, it’s been a treat for fans of the sport and the rest of the world at large. With so many iconic moments, some have left a mark in boxing history. Very few boxers could stun a crowd quite like Mike Tyson, and the following moments are proof.
7. Mike Tyson’s Controversial Post-Prison Bout Against Orlin Norris (1999)
The bout between Mike Tyson and Orlin Norris on October 23, 1999, at the MGM Grand Garden Arena, was a controversial one. Tyson, the former undisputed heavyweight champion, entered the ring with a 46–3 record. He faced Norris, a former WBA Cruiserweight champion with a 50–5 record. The match was Tyson’s second fight following a comeback after serving time in prison from 1992 to 1995.
Despite the anticipation generated ahead of the match, it ended abruptly and contentiously. After the first round bell, Tyson landed a punch that knocked Norris down, injuring his knee. This was despite his looking calm and in control throughout the round. Regardless, the blow, deemed a foul since it was delivered after the round had ended, resulted in the match being stopped and declared a no-contest before the second round could begin. The aftermath was expectedly chaotic, with debates over Tyson’s intent and the possibility that Norris might have lied about the injury. For people who believed Tyson had intentionally landed the post-bell punch, this incident added another layer of infamy to Tyson’s career.
6. The Aggressive Defeat Of Larry Holmes (1988)
In the winter of 1988, on January 22nd, Mike Tyson, the then-reigning heavyweight champion, faced off against Larry Holmes, a former champion staging a comeback. The bout, held at Trump Plaza in Atlantic City, was billed as “Heavyweight History.” By this time, Tyson was already known for his aggressive style and ferocity. He was at the peak of his career with a 32-0 record, including 28 knockouts. Holmes, on the other hand, was from a different time in boxing history. Nicknamed “The Easton Assassin,” he was a seasoned fighter with a 48-2 record and a formidable jab that humbled the great Muhammad Ali in 1980.
The fight was a clash between Tyson’s raw, youthful aggression against Holmes’ experienced, technical prowess. The winner was clear very quickly. Even as Holmes countered him perfectly, none of it seemed to matter, as Tyson hammered him with powerful combinations almost immediately after they entered the ring. In the fourth round, he delivered a devastating right hook that dropped Holmes for a third time. This led the referee to stop the fight and award Tyson the victory by technical knockout.
5. Mike Tyson Makes History Against Trevor Berbick (1986)
On the night of November 22, 1986, a young Mike Tyson, barely out of his teens and already a force to be reckoned with, stepped into the ring against Trevor Berbick. Tyson, freshly trained and brimming with confidence, already had a head-turning 27-0 record, with 25 knockouts. That year alone, he had demolished his opponents in a 12-0 run. That night at the Las Vegas Hilton, 20-year-old Tyson was dressed in his (now) signature black trunks and shoes, draped with a simple white towel, ready to show the world the making of a legend.
Meanwhile, Trevor Berbick was the recently crowned WBC heavyweight champion. He had earned his title through grit and experience, notably defeating Muhammad Ali in the legend’s final fight and edging out Pinklon Thomas by a narrow points decision. However, the stage was set for a changing of the guard. The fight was swift and decisive. Tyson, a whirlwind of power and aggression, overwhelmed Berbick, who found himself outmatched and outclassed. The second-round technical knockout was a statement: Tyson was not just a contender but a champion. He became the youngest heavyweight title holder in history. All it took was 2 minutes 35 seconds.
4. The 91-Second Match Against Michael Spinks (1988)
The Tyson v. Spinks battle took place on June 27, 1988, at the Convention Hall in Atlantic City. Dubbed “Once and For All” by promoters, it marks one of the most petrifying Tyson matches of all time. Michael Spinks, nicknamed “Jinx,” held a 31-0 record with 21 knockouts. He was a lineal champion that conquered legends like Larry Holmes. Meanwhile, at the time, Tyson was the youngest heavyweight champion ever, and was a wrecking ball with a 34-0 record with 30 knockouts. He was also a very humble WBA, WBC, and IBF title holder. Everyone was hankering to see this match of legends.
By the time the bell rang, Tyson charged into the ring like a bull and pulled off the impossible. Within 91 seconds, Spinks was down and out on the canvas. People were dumbfounded, and some were even annoyed. Like a cherry on the cake, the 91-second match would become the richest fight in boxing history, grossing an astounding $70 million, of which Tyson earned a record purse of around $22 million and Spinks won $13.5 million.
3. Lennox Lewis Asserts His Dominance In The Ring (2002)
On June 8, 2002, Mike Tyson and Lennox Lewis faced off at the Pyramid Arena in Memphis. The fight was a significant heavyweight title match, with Lewis defending his WBC, IBF, IBO, and The Ring titles against Tyson. It would be Tyson’s final chance to reclaim the world title, and he was so hungry for it. In fact, the match had to be moved to Memphis after Tyson was denied a license in Nevada due to a press conference brawl between him and Lewis in NYC.
There was a thick cloud of tension in the air when the match began. In the opening round, Tyson’s left hook quickly found its mark, but Lewis countered with powerful combinations, one of which opened a cut above Tyson’s right eye. He then continued to seize control, raining devastating blows until the seventh round. In the eighth, a visibly tired Tyson hit the canvas, struggling to rise after a heavy right cross from Lewis. At some point in the match, the great Iron Mike Tyson retreated to the corners and screamed, “I’m in pain!” By the eighth round, Lewis’s dominance was clear. At the 2:25 mark, the referee called it, and Tyson was knocked out.
2. Mike Tyson’s First-Ever Loss Against Buster Douglas (1990)
On February 11, 1990, the Tokyo Dome bore witness to one of the most jaw-dropping occurrences in the boxing world. Mike Tyson, the five-year undefeated and undisputed heavyweight champion, stepped into the ring against James “Buster” Douglas. Specifically, Douglas was a 42:1 record holder who was an underdog, especially compared to Tyson. Although the odds were stacked against Douglas, fate had other plans.
Tyson, known for his ferocious power, was expected to dispatch Douglas swiftly, much like his portfolio showed. However, the fight unfolded differently. Tyson managed to knock Douglas out for 13 seconds in the eighth round, but that was not enough to stop his opponent. Standing at 6 ft 4, Douglas used his reach advantage to keep Tyson at bay. In the tenth round, against all odds, Douglas unleashed a combination that sent Tyson crashing to the canvas. The referee counted, and the impossible had happened: Tyson was knocked out.
1. The Infamous “Bite Fight” Against Evander Holyfield (1997)
Mike Tyson vs. Evander Holyfield II is a fight that remains etched in boxing history forever. The rematch took place on June 28, 1997, at the MGM Grand Garden Arena in Paradise, Nevada. Holyfield, the defending WBA Heavyweight Champion, had shocked Tyson seven months earlier with an 11th-round knockout. Importantly, this fight coincided with Tyson’s post-prison era, when he was quite emotionally strained. All this meant that the lead-up to the fight made it one of the most anticipated sporting events of the year.
When D-day came, Holyfield managed to dominate Tyson in the earlier rounds. Tyson, frustrated by a headbutt from Holyfield that caused a large cut under his right eye, aggressively sought to retaliate. And so, in the third round, right as the two grappled in the ring, Tyson bit off over an inch of Holyfield’s right ear and spat it out. The fight resumed, but it only lasted for a while because Tyson also bit Holyfield’s left ear.
Tyson was disqualified from the match and lost his boxing license, although it was later reinstated. An employee working at the MGM Arena picked up the detached ear, placed it on ice, and was transported to a hospital for reattachment. Holyfield and his trainer, Tim Hallmark, would later reveal that the detached ear was lost in the ambulance. As a result, Holyfield still wears the scars to this day, as the cartilage never grew back.
The “Bite Fight” has been one of the most referenced events in mainstream boxing history. It remains a defining trait of Mike Tyson’s public persona. For example, in 2022 Tyson’s company Tyson 2.0 launched “Mike Bites,” a line of marijuana-infused ear-shaped gummies…with part of the ear missing. However, without a doubt, it’s the most infamous boxing match in history.
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