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)
Max Schmeling vs. Joe Louis (Source: History.com)
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)
Randy Turpin vs. Sugar Ray Robinson (Source: The Fight City)
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)
Lloyd Honeyghan vs. Donald Curry (Source: The Fight City)
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)
Fritzie Zivic vs. Henry Armstrong (Source: The Fight City)
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)
Kirkland Laing vs. Roberto Durán (Source: FightPost)
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)
Antonio Tarver hits Roy Jones Jr. in a WBC and IBO Light Heavyweight championship fight. (Source: Jed Jacobsohn/Getty Images)
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)
Michael Spinks vs. Larry Holmes (Source: The Fight City)
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)
Carlos Baldomir charges at Zab Judah during their undisputed World Welterweight Championship fight. (Source: Al Bello/Getty Images)
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 upsetsRankFightYearWinnerLoserNotable detail1James Douglas vs. Mike Tyson1990Buster DouglasMike TysonDouglas, a 42–1 underdog, knocked out Tyson in the 10th round in Tokyo, in one of the biggest upsets in boxing history.2Max Schmeling vs. Joe Louis1936Max SchmelingJoe LouisSchmeling exploited Louis’s jab flaw, winning by KO in the 12th round. Louis avenged the loss two years later.3Hasim Rahman vs. Lennox Lewis2001Hasim RahmanLennox LewisRahman, a 20–1 underdog, knocked out Lewis in the 5th round, shocking the boxing world.4Andy Ruiz Jr. vs. Anthony Joshua2019Andy Ruiz Jr.Anthony JoshuaRuiz, 25–1 underdog, stopped Joshua in the 7th round in Madison Square Garden.5Leon Spinks vs. Muhammad Ali1978Leon SpinksMuhammad AliSpinks, with only 7 pro fights, won a split decision over Ali to become heavyweight champion.6Randy Turpin vs. Sugar Ray Robinson1951Randy TurpinSugar Ray RobinsonTurpin broke Robinson’s 91-fight winning streak, winning the middleweight title by decision.7James Braddock vs. Max Baer1935James BraddockMax BaerBraddock, once struggling financially, captured the heavyweight title with a unanimous decision.8Lloyd Honeyghan vs. Donald Curry1986Lloyd HoneyghanDonald CurryHoneyghan defeated the undisputed welterweight champion Curry by TKO in round 6.9Evander Holyfield vs. Mike Tyson1996Evander HolyfieldMike TysonHolyfield absorbed Tyson’s early onslaught and stopped him in the 11th round to reclaim the heavyweight title.10Muhammad Ali vs. George Foreman1974Muhammad AliGeorge ForemanAli used the “Rope-a-Dope” strategy to tire Foreman, knocking him out in the 8th round in the “Rumble in the Jungle”.