The boxing world has always thrived on drama, but some nights leave fans stunned and pundits speechless. In the blink of an eye, a dominant champion can fall, rewriting history and reshaping legacies in ways few predict.

Upsets in the ring are more than just shocking results—they are defining moments. From underdogs defying odds to veteran fighters facing unexpected defeats, these bouts reveal the unpredictable heartbeat of the sport.

Boxing history is filled with matches where expectations were shattered. The roar of the crowd, the stunned silence and the scramble for headlines all capture why these monumental upsets and brutal fights remain etched in memory.

James Douglas vs. Mike Tyson (1990)

On February 11, 1990, Mike Tyson entered the ring as an undefeated, undisputed heavyweight champion, a force of nature who had demolished opponents with frightening ease. But in Tokyo, Buster Douglas delivered a performance that would forever alter the sport’s landscape.

Douglas, a 42-to-1 underdog, withstood a knockdown in the eighth round and came back to stop Tyson in the tenth. The upset was so seismic that it is still regarded as the greatest in boxing history.

Max Schmeling vs. Joe Louis (1936)

In 1936, the world was captivated by the undefeated American champion Joe Louis, who was poised to become a symbol of hope during the Great Depression. But in a stunning turn, German boxer Max Schmeling exploited a flaw in Louis’s technique, countering his jab with a right hand that knocked him out in the 12th round. The defeat was a propaganda victory for Nazi Germany, but Louis would avenge the loss two years later with a first-round knockout.

Hasim Rahman vs. Lennox Lewis (2001)

Lennox Lewis was the undisputed heavyweight champion, preparing for a lucrative bout with Mike Tyson. But on April 22, 2001, Hasim Rahman, a 20-to-1 underdog, shocked the world by knocking out Lewis in the fifth round. The upset was so unexpected that it left fans and analysts alike questioning the sport’s unpredictability.

Andy Ruiz Jr. vs. Anthony Joshua (2019)

In June 2019, Anthony Joshua was the unified heavyweight champion, a towering figure with an undefeated record. But in Madison Square Garden, Andy Ruiz Jr., a late replacement and 25-to-1 underdog, delivered a stunning performance, knocking Joshua down four times before stopping him in the seventh round. The upset was so significant that it was compared to Buster Douglas’s victory over Mike Tyson.

Leon Spinks vs. Muhammad Ali (1978)

In 1978, Muhammad Ali was the reigning heavyweight champion, but 25-year-old Leon Spinks, with only seven professional bouts, faced him for the title. In a bout that defied expectations, Spinks won a split decision, becoming the heavyweight champion. The victory was so surprising that it earned Spinks a spot on the cover of Sports Illustrated.

Randy Turpin vs. Sugar Ray Robinson (1951)

Sugar Ray Robinson, known as the greatest pound-for-pound fighter, was on a 91-fight winning streak when he faced British boxer Randy Turpin in 1951. In a bout that stunned the boxing world, Turpin outboxed Robinson, winning the middleweight title in a unanimous decision. The upset was so unexpected that it left fans and analysts alike in disbelief.

James Braddock vs. Max Baer (1935)

James “Cinderella Man” Braddock was a struggling boxer, once ranked among the top contenders, who had fallen into poverty. But in 1935, he faced the formidable Max Baer for the heavyweight title. In a bout that defied expectations, Braddock won a unanimous decision, capturing the championship and becoming a symbol of hope during the Great Depression.

Lloyd Honeyghan vs. Donald Curry (1986)

In 1986, Donald Curry was the undisputed welterweight champion, hailed as one of the best pound-for-pound fighters. But in a bout that shocked the boxing world, British challenger Lloyd Honeyghan defeated Curry by technical knockout in the sixth round. The upset was so significant that it was dubbed the “miracle win” and is considered one of the greatest victories in British boxing history.

Evander Holyfield vs. Mike Tyson (1996)

In 1996, Mike Tyson was the undisputed heavyweight champion, known for his ferocious power and undefeated record. Evander Holyfield, a former cruiserweight champion, was seen as a stepping stone for Tyson’s return to the top.

However, Holyfield had other plans. He absorbed Tyson’s early onslaught and began to dominate the later rounds with superior technique and resilience. In the 11th round, Holyfield stopped Tyson, shocking the world and reclaiming the heavyweight title.

Muhammad Ali vs. George Foreman (1974)

The “Rumble in the Jungle” in 1974 pitted the undefeated heavyweight champion George Foreman against the former champion Muhammad Ali. Foreman was known for his brutal knockout power, while Ali was considered past his prime.

In a strategy that became legendary, Ali allowed Foreman to tire himself out by leaning against the ropes and absorbing punches. In the eighth round, Ali unleashed a series of quick combinations, knocking Foreman out and regaining the heavyweight title.

Fritzie Zivic vs. Henry Armstrong (1940)

On October 4, 1940, at Madison Square Garden, Fritzie Zivic faced the formidable Henry Armstrong for the world welterweight title. Armstrong, known for his relentless pressure and punching power, was expected to dominate.

However, Zivic employed a masterful defensive strategy, frustrating Armstrong throughout the 15-round bout. In the final round, Zivic scored a knockdown, securing a unanimous decision victory and the welterweight title.

Sugar Ray Leonard vs. Marvin Hagler (1987)

In 1987, Marvelous Marvin Hagler was the undisputed middleweight champion, known for his aggressive style and dominance in the ring. Sugar Ray Leonard, who had been retired for over three years, returned to challenge Hagler.

Despite doubts about his readiness, Leonard showcased exceptional speed and ring intelligence, outpointing Hagler over 12 rounds. The split decision victory was controversial but marked one of the most significant upsets in boxing history.

Kirkland Laing vs. Roberto Duran (1982)

On September 4, 1982, in Detroit, Kirkland Laing faced the legendary Roberto Duran, a two-division world champion. Duran, known for his ferocious fighting style, was expected to dominate the bout.

However, Laing employed an unorthodox, hands-down approach and constant movement, frustrating Duran throughout the 10-round contest. Despite a controversial split decision, Laing was awarded the victory, earning the upset of the year honors from The Ring magazine.

Frankie Randall vs. Julio César Chávez (1994)

Julio Cesar Chavez, the undefeated WBC super lightweight champion, was considered one of the best pound-for-pound fighters in the world. On January 29, 1994, Frankie Randall, a skilled and determined challenger, faced Chavez in Las Vegas.

In a bout that defied expectations, Randall outboxed Chavez, scoring a knockdown in the 11th round. The split decision victory for Randall ended Chavez’s 13-year unbeaten streak and was hailed as one of the biggest upsets in boxing history.

Antonio Tarver vs. Roy Jones Jr. (2004)

Roy Jones Jr., widely regarded as the best pound-for-pound boxer at the time, faced Antonio Tarver on November 8, 2004, in Las Vegas. Jones, coming off a controversial decision victory over Tarver earlier in the year, was expected to dominate the rematch.

However, Tarver stunned the boxing world by knocking out Jones in the second round with a single left hand. The knockout was so unexpected that it left fans and analysts alike in disbelief.

George Foreman vs. Michael Moorer (1994)

In 1994, George Foreman, at 45 years old, was attempting a comeback against the undefeated heavyweight champion Michael Moorer. Moorer controlled the first nine rounds with his jab and was ahead on the scorecards.

However, Foreman, known for his devastating power, landed a massive right hand in the 10th round that floored Moorer, making Foreman the oldest heavyweight champion in history. The upset was so unexpected that it was compared to Buster Douglas’s victory over Mike Tyson.

Michael Spinks vs. Larry Holmes (1985)

On September 21, 1985, Michael Spinks achieved a historic feat by becoming the first reigning light-heavyweight champion to win a piece of the World Heavyweight Crown.

Facing the formidable Larry Holmes, who was undefeated at 48–0, Spinks employed a tactical approach that outmaneuvered Holmes, securing a unanimous decision victory. This upset not only disrupted Holmes’ quest for a record-breaking 49th consecutive win but also marked a significant milestone in boxing history.

George Foreman vs. Joe Frazier (1973)

The “Sunshine Showdown” on January 22, 1973, saw George Foreman face the reigning heavyweight champion Joe Frazier in Kingston, Jamaica. Foreman, known for his devastating punching power, overwhelmed Frazier in just two rounds, delivering six knockdowns and securing a technical knockout. This dominant performance not only earned Foreman the heavyweight title but also stunned the boxing world, showcasing his formidable prowess.

Iran Barkley vs. Thomas Hearns (1988)

On June 6, 1988, in Las Vegas, Iran Barkley faced the renowned Thomas “The Hitman” Hearns for the WBC middleweight title. Despite being an underdog, Barkley delivered a shocking third-round knockout, earning the “Upset of the Year” accolade from The Ring magazine. This victory not only secured Barkley the middleweight championship but also highlighted the unpredictable nature of boxing.

Carlos Baldomir vs. Zab Judah (2006)

In a surprising turn of events on January 7, 2006, Carlos Baldomir, an unheralded challenger from Argentina, defeated the undisputed welterweight champion Zab Judah at Madison Square Garden.

Baldomir’s relentless pressure and strategic approach led to a unanimous decision victory, with scores of 115–113, 114–113, and 115–112. This upset not only earned Baldomir the WBC and The Ring titles but also disrupted plans for a high-profile bout between Judah and Floyd Mayweather Jr.

Top 10 biggest upsets

The 1980s witnessed a golden era in boxing, defined by the fierce rivalries of the “Four Kings“—Sugar Ray Leonard, Marvin Hagler, Thomas Hearns and Roberto Duran. These four legends not only dominated the ring but also embodied the sport’s raw intensity and drama.

Each bout between these titans was a spectacle, characterized by brutal exchanges, strategic prowess and moments of sheer willpower. From relentless aggression to calculated precision, their contrasting styles created a dynamic that kept audiences on the edge of their seats.

Blood, sweat and unyielding determination were constants in every clash. Rings shook with the force of their power punches, punishing jabs, and ferocious inside attacks. Every encounter tested the limits of endurance, leaving legacies etched into boxing history and securing their place in the greatest fights of all time.

Sugar Ray Leonard vs. Roberto Duran I (1978) – “The Brawl in Montreal”

On June 20, 1980, at Montreal’s Olympic Stadium, Sugar Ray Leonard faced Roberto Duran in a bout that would ignite one of boxing’s most legendary rivalries. Leonard, known for his speed and finesse, entered the ring with an undefeated record of 27–0, while Duran, the reigning WBC welterweight champion, was a formidable force with a record of 71–1.

The fight was a clash of styles—Leonard’s agility against Duran’s relentless aggression. Duran’s pressure and inside fighting overwhelmed Leonard, leading to a unanimous decision victory for Duran with scores of 146–144, 145–144, and 148–147. This bout marked Leonard’s first professional loss and set the stage for their iconic trilogy.

Sugar Ray Leonard vs. Roberto Duran II (1980) – “The Super Fight”

The highly anticipated rematch took place on November 25, 1980, at the Louisiana Superdome in New Orleans. Leonard adopted a new strategy, using his speed and movement to outbox Duran, who had previously dominated him.

In the eighth round, Leonard taunted Duran and landed a clean jab, causing Duran to turn away and quit the fight, famously saying “No más” (No more). Leonard won by technical knockout, regaining the WBC welterweight title.

Sugar Ray Leonard vs. Roberto Duran III (1989) – “Uno Más”

The final chapter of their rivalry occurred on December 7, 1989, at The Mirage in Las Vegas. Leonard, now a five-division world champion, faced Duran, who was attempting to become a five-division champion himself.

Leonard dominated the fight, landing 227 punches compared to Duran’s 84. All three judges scored the bout in favor of Leonard with scores of 120–110, 119–109, and 116–111. This victory solidified Leonard’s legacy and concluded one of boxing’s most storied rivalries.

Sugar Ray Leonard vs. Thomas Hearns I (1981) – “The Showdown”

On September 16, 1981, Sugar Ray Leonard and Thomas Hearns faced off at Caesar’s Palace in Las Vegas for the undisputed welterweight championship. Hearns, known for his powerful jab and knockout ability, built an early lead.

However, Leonard’s resilience and strategy turned the tide. In the 14th round, Leonard unleashed a combination that sent Hearns through the ropes, leading to a stoppage and a TKO victory for Leonard. This bout is remembered for its dramatic momentum shifts and Leonard’s determination.

Marvin Hagler vs. Roberto Duran (1983)

On November 10, 1983, at Caesar’s Palace, Marvin Hagler defended his undisputed middleweight titles against Roberto Duran. Duran, moving up in weight, faced the challenge of Hagler’s relentless pressure and southpaw stance.

The fight was a tactical battle, with Hagler’s power and Duran’s skill on full display. Hagler won by unanimous decision, but Duran’s performance earned him respect in the higher weight class.

Thomas Hearns vs. Roberto Duran (1984) – “Malice at the Palace”

On June 15, 1984, Thomas Hearns and Roberto Duran met at Caesar’s Palace for the WBC and The Ring super welterweight titles. Hearns’ height and reach advantage were evident as he dominated the fight.

In the second round, Hearns knocked Duran down three times, leading to a stoppage and a TKO victory for Hearns. This bout showcased Hearns’ power and established him as a dominant force in the division.

Marvin Hagler vs. Thomas Hearns (1985) – “The War”

On April 15, 1985, Marvin Hagler and Thomas Hearns faced each other in a bout that would become known as “The War.” From the opening bell, both fighters exchanged powerful punches in a non-stop barrage.

The first round is considered one of the greatest in boxing history. Hagler eventually stopped Hearns in the third round, but the fight’s intensity and ferocity left an indelible mark on the sport.

Sugar Ray Leonard vs. Marvin Hagler (1987) – “The Super Fight”

On April 6, 1987, Sugar Ray Leonard and Marvin Hagler met in a highly anticipated middleweight championship bout at Caesar’s Palace. Leonard, coming out of retirement, faced Hagler, the reigning champion.

The fight was a tactical battle, with Leonard using his speed and movement to outpoint Hagler. In a controversial split decision, Leonard was awarded the victory, marking the end of Hagler’s 12-year reign as middleweight champion.

Who among the Four Kings had the most wins and losses?

The Four Kings—Sugar Ray Leonard, Marvin Hagler, Thomas Hearns and Roberto Duran—were not only contemporaries but also fierce rivals who defined an era of boxing. Their careers were marked by numerous bouts against each other, each leaving an indelible mark on the sport’s history.

Among them, Roberto Duran boasts the highest number of wins, with a professional record of 103 victories, 16 losses and 0 draws. Known as “Manos de Piedra” (“Hands of Stone”), he secured 70 of his wins by knockout. His aggressive style, ferocity and resilience made him a dominant force in the ring and a legend.

He also holds the highest number of losses among the Four Kings, with 16 defeats. Despite this, his legacy is far from diminished. His fearless approach and ability to battle elite opponents across decades earned him enduring respect and admiration from fans and fellow fighters alike.

Sugar Ray Leonard and Marvin Hagler both had impressive records, with Leonard achieving 36 wins, 3 losses and 1 draw, and Hagler securing 62 wins, 3 losses and 2 draws. Leonard’s versatility and charisma made him a fan favorite, while Hagler’s relentless pressure and southpaw stance earned him respect as one of the greatest middleweights of all time.

Thomas Hearns concluded his career with 61 wins, 5 losses and 1 draw. Known as “The Hitman”, he was celebrated for his devastating punching power and his ability to dominate across multiple weight classes, making him one of the most feared and respected fighters of the era.

These statistics not only highlight the individual achievements of each boxer but also underscore the intense competition and high stakes that characterized the Four Kings era. Their rivalries pushed each fighter to their limits, contributing to the rich tapestry of boxing history.

Canelo, boxing’s reigning undisputed super-middleweight champion, will face a formidable challenger in Crawford—who is aiming to become the first male fighter to claim undisputed titles in three weight divisions. It’s a matchup that transcends weight classes and generations, pitting two of the sport’s most cerebral and technically gifted athletes against each other on the biggest stage.

Shortly after Canelo’s recent victory over William Scull in Riyadh—a win that didn’t fully impress critics—the sport’s attention shifted to Crawford, who had been waiting in the wings. And now, as the promotional engines begin to roar, one legendary voice has already made his opinion clear.

Duran’s prediction

Panamanian icon Roberto Duran, never one to mince words, was asked about the fight during a recent interview with Fight Hub TV. Without hesitation, he laid out what Crawford must do to pull off the historic upset.

“It’s a tough fight, but it depends on how Crawford comes in,” Duran stated. “He needs to box and brawl, keep confusing Canelo. Brawl, then box when Canelo expects a brawl. Next round, box when he expects you to brawl, keep him confused and you can win the fight vs. Canelo.”

It’s a veteran strategist’s perspective—one that emphasizes rhythm disruption, mental warfare, and calculated shifts in style. Duran’s assessment hinges on Crawford’s ability to be unpredictable, a quality that has defined his rise through the welterweight and light-middleweight divisions.

Crawford’s legacy and the leap to 168

Crawford, known as “Bud,” has never competed above 154 pounds. His last outing came in August, when he handed previously unbeaten Israil Madrimov his first professional loss via unanimous decision in Los Angeles. That victory earned him the WBA light-middleweight crown and set the stage for this monumental leap.

Now, as he prepares to challenge Canelo at 168, questions remain. Can Crawford carry his power and speed into the super-middleweight division? As September draws near, the boxing world will be watching closely—not just to see if Crawford can dethrone Canelo, but to witness whether a once-in-a-generation fighter can defy history once again.

In a 2020 conversation with the World Boxing Council (WBC), Duran explained that he felt closely connected to the style of the man he considers the best of all time: Muhammad Ali.

Duran went even further and shared his personal Top 10 list of the greatest boxers in history, which includes several iconic names — and reflects his deep connection with Mexican boxing. Among them, he ranked Julio Cesar Chavez fourth, placing the Mexican legend ahead of some other all-time greats.

Interestingly, Duran’s list excludes modern stars like Floyd Mayweather Jr. and Canelo Alvarez, a decision that may surprise some fans. Still, the Panamanian icon made clear that choosing only ten names means some incredible talents will inevitably be left out.

Duran: A legacy that spans generations

Roberto Duran, considered by many the greatest lightweight in history, competed from the 1970s into the early 2000s. Known for his tenacity and power, he fought from 135 to 168 pounds, squaring off against the best in each division. His career left an indelible mark on the sport, and even at age 73, Duran remains a revered figure in boxing history.

Asked whether he’d ever return to the ring, the Hall of Famer joked: “I’m already in bad shape hahaha, but yes, if asked, sure I’d get up there in the ring in a fight for charity… I’d do my best to evade big punches (laughs).”

Roberto Duran’s top 10 greatest boxers of all time

“On my list, I’d mention greats such as Muhammad Ali, Rocky Marciano. Also, Marvin Hagler, Julio Cesar Chavez, Sugar Ray Leonard, Joe Frazier, Tommy Hearns, Ruben Olivares,” Duran said.

Beyond his return to the spotlight, Tyson has left an indelible mark on the sport—not just for his devastating knockouts, but also for his outspoken admiration of other great fighters.

An international boxing phenomenon and an icon of the 1990s and early 2000s, Tyson is widely regarded as one of the greatest fighters in history, if not the greatest. However, Tyson himself has a different opinion. A few years ago, he boldly revealed who he believes deserves the title of “Best of All Time.”

Who does Mike Tyson consider the best boxer in history?

Despite being hailed as the greatest boxer of his generation, Tyson has been clear about who he believes holds the crown. In an interview with Complex, Tyson shared his respect for two legendary fighters:

“I love Roberto Durán and Muhammad Ali,” Tyson said. “Ali is the greatest fighter that ever lived. I have to go with him, yeah.”

What is Mike Tyson’s boxing record?

At 58 years old, Mike Tyson boasts an impressive professional record of 57 fights, with 50 wins and only 7 losses. Before stepping into the ring with Jake Paul, Tyson hadn’t fought since June 11, 2005. That match marked his retirement from professional boxing after a technical knockout loss to relatively unknown fighter Kevin McBride.

As a pure Panamian, Duran has the frankness under his skin. The mightyManos de Piedradoes not know about politics when it comes to saying his truth. After all, he must know “something” about the fists sport after holding 119 fights and winning titles in four different divisions.

This time, Roberto Duran touched a polemic and current subject: is Canelo Alvarez really the present name and face of boxing oris he just a marketing illusion? How big is the Mexican legacy so far? Where is Saul in comparison to other fighting legends? As the historical Michael Buffer says: “Let’s get ready to rumble!“.

Duran’s opinion about Canelo Alvarez’s career

In an interview forES News,Hands of stoneconfessed his admiration for Canelo’s achievements so far and defined the place the Pound for Pound king occupies not only right now, but in the list of Mexican greatestof all time.

“I feel happy for Canelo. All that he is doing so far is for the good of his career and the good of Mexico. He is the boxer of the moment, a respected idol. Everybody has to accept that. Julio Cesar Chavez is a legend; Canelo is already another legend, it does not matter if Mexico refuses to accept it. How many titles has Chavez won? Three. And Canelo has already gotten four, so he is even bigger“.

Even more, Roberto Duran defended the legacy of Alvarez: “Canelo is giving Mexico a lot of fame nowadays, and he is earning much more money than anyone. Even more than Julio Cesar Chavez and me. The ones who speak badly about Canelo are just envious” concluded the mighty Panamian.