The 15 Greatest Boxing Fights in History

Boxers fighting

Boxing is a sport of will, timing, and intelligence in the ring. Two athletes enter the arena knowing their ego and reputation could be cut-down swiftly by an expertly timed right hook, yet they take the risk anyway. We respect them because they put everything on the line to prove their worth and skills. It’s one of the most thrilling sports to watch, and  sometimes two titans collide to put on a spectacular show that winds up being a classic bout.

There are plenty of amazing boxing matches that took place throughout the history of the sport, and many men have displayed the evolution of the sweet science with heart. After careful consideration and tons of shadowboxing while watching some of the most memorable bouts, we’ve put together a list of the greatest boxing fights in history for your enjoyment. Watching these particular fights will stir the fire in you to lace up some leather boxing gloves and find out what you’re capable of in the ring. At the very least, the fights will inspire you to excel in your current endeavor. Take a seat, grab a pen and notepad, and enjoy the very best matchups in the sport of boxing.

Top 15 Greatest Boxing Fights in History

1. Joe Louis vs. Billy Conn

After defending his title against punching bags with limbs, Joe Louis ran into a fighter who would put up a real challenge. Conn was a talented pugilist with a cocky swagger who surrendered his lightweight heavyweight title to move up and fight Louis. The Irishman put up a great fight despite giving up 25 pounds, as he landed flurries and worked his jab with technical prowess. In the 12th round, Conn swung a left hook that landed flush on the champ’s chin, causing him to clinch so he wouldn’t hit the canvas. However, Louis, who is known as one of the best heavyweight finishers in the sport’s history, turned up the heat and sent Conn to the canvas to win the fight by knockout.

Date: June 18, 1941

Winner: Joe Louis (KO)

Title: n/a

2. Sugar Ray Robinson vs. Jake La Motta

Nicknamed Raging Bull, Jake La Motta brought hell with him every time he stepped into the ring. His fights with Sugar Ray Robinson were epic, to say the least, but the most notable is the St. Valentine’s Day Massacre. Taking place at Chicago Stadium, the 15-round fight for the middleweight title. Both boxers put on quite a show, but it was Robinson who ended up victorious when he landed blood-gushing blows without pause in the 13th round. However, La Motta never went down from the shower of fists. La Motta said, “If the referee had held up another 30 more seconds, Sugar Ray [Robinson] would have collapsed from hitting me.” The Raging Bull was undeniably a beast among men, but so was Robinson.

Date: February 14, 1951

Winner: Sugar Ray Robinson (TKO)

Title: St. Valentine’s Day Massacre

3. Muhammad Ali vs. George Foreman

At the time, Big George Foreman was the undefeated heavyweight champion of the world, and Muhammad Ali was coming in as the challenger with many believing Foreman would defeat the former champ. Ali utilized his rope-a-dope strategy to perfection, leaning on the ropes and covering up while Foreman threw shots at his arms and body, tiring himself out in the process. Most of Foreman’s punches were missing or deflected by Ali, and G.O.A.T sent straight punches to Foreman’s mug. Sapped of energy and sporting a bloated face, Foreman ate one too many crosses, looking worn-out by the fifth round. In classic Ali fashion, the legend taunted Foreman saying, “They told me you could punch, George!” Just before the end of the eight-round, Ali put Foreman down, ending the bout by knockout.

Date: October 29, 1974

Winner: Muhammad Ali (KO)

Title: The Rumble in the Jungle

4. Muhammad Ali vs. Joe Frazier

After Muhammad Ali and Joe Frazier each one a fight, the two entered a rubber match to complete the trilogy. Dubbed the “Thrilla in Manila,” the fight is one of the most praised displays of heart in any combat sport. The legacy-deciding fight pitted these to titans against each other one last time. No matter what Ali threw at Frazier, the machine kept coming, keeping his bullish style, taking control of the fight in the middle rounds. However, Ali poured his heart into the 13th and 14th rounds, burying Frazier in punches as if the world depended on it. Frazier’s trainer Eddie Futch put an end to the fight, allowing Ali to win by TKO. Futch told Frazier “No one will ever forget what you did here today.”

Date: October 1, 1975

Winner: Muhammad Ali (TKO)

Title: Thrilla in Manila

5. Roberto Duran vs. Sugar Ray Leonard

The roles of hero and villain were never as clear in boxing as they were with Sugar Ray Leonard and Roberto Duran. Leonard was the clean-cut boxing golden boy, and Duran was seen as a thug in and out of the ring. At the time, the fighters were considered the best in the world. The match was captivating because of their contrasting styles. Leonard was all finesse, and Duran came in as a brawler. Leonard went against his own style and tried standing his ground against “Hands of Stone” Duran, and he paid for it, as Duran swarmed him. Leonard started to work his counters in the fifth round, and the rest of the match was close. Most of the fight was a toe-to-toe affair, which is where Duran feels right at home, leading him to the victory.

Date: June 20, 1980

Winner: Roberto Duran (unanimous decision)

Title: The Brawl in Montreal

6. Larry Holmes vs. Gerry Cooney

A fight made extreme by overtly racial elements, the Larry Holmes and Gerry Cooney bout had plenty of tension surrounding it. Cooney, an Irish-American, was dubbed the “Great White Hope,” as he was featured on the cover of Time and had a phone installed in his dressing room so President Ronald Reagan could call him if he won the fight. On the other hand, champion Holmes did not get any special treatment. There was even a report that white supremacist groups had agents ready to shoot Holmes right when he entered the ring. Keeping his cool, Holmes schooled Cooney and delivered a barrage of blows in the thirteenth round, sending him to the canvas. Cooney’s trainer Victor Valle stopped the fight, realizing his athlete had nothing left to give.

Date: June 11, 1982

Winner: Larry Holmes (TKO)

Title: n/a

7. Marvin Hagler vs Tommy Hearns

Marvelous Marvin Hagler and Tommy “The Hitman” Hearns were both tremendous boxers with monstrous power punches. As advertised, this fight was an all-out war between two heavy hitters. It only lasted three rounds, but delivered action every second, as both men saw red. Hagler’s savage blows managed to dismantle Hearns in the third round, dropping him to the floor. Although Hearns was able to get up and beat the count, the ref called the fight, leading to a TKO victory for Hagler. Hearns was beaten so badly, he had to e carried into the locker room.

“The War” was a bombs-away match that delivered the goods whether you’re a boxing fan or not.

Date: April 15, 1985

Winner: Marvin Hagler (TKO)

Title: The War

8. Mike Tyson vs. Trevor Berbick

In his prime, Mike Tyson was an absolute monster who destroyed everyone in the heavyweight division. Most of his fights were more like executions than actual challenges. Arguably his most memorable match is the one against Trevor Berbick. Berbick entered the ring as the current champ, but Tyson blasted him and never let up. A right to the body followed up by a left hook to the head dropped Berbick to the canvas in the second round. Berbick tried to muster up the strength to get up twice but ultimately collapsed. That day Tyson became the youngest heavyweight champion in history. It was an even sweeter victory for Tyson since Berbick was the man to beat Muhammad Ali, who’s Tyson’s hero, into retirement.

Date: November 22, 1986

Winner: Mike Tyson (TKO)

Title: Judgement Day

9. Sugar Ray Leonard vs. Marvin Hagler

Sugar Ray Leonard decided to come out of a three-year retirement to fight Marvin Hagler at Caesars Palace with Hagler being the betting favorite. Although he’s a natural southpaw, Hagler gave Leonard a different look by opening the fight in an orthodox stance, yet later switched to southpaw after Leonard one the first couple of rounds. Leonard was slick, but Hagler landed his jab persistently, diffusing Leonard’s counter flurries. Both fighters turned in incredible performances, but Leonard won by split decision, which is hotly disputed to this day. Before this match took place, Hagler was on an 11-year undefeated streak. After the fight, Hagler claimed that Leonard said, “you beat me, man,” which Leonard denies.

Date: April 6, 1987

Winner: Sugar Ray Leonard (split decision)

Title: n/a

10. Mike Tyson vs. Michael Spinks

Before this fight went down, Iron Mike Tyson and Michael Spinks were both undefeated, and each man had a claim to being the legitimate heavyweight champion of the world. Some experts said that Spinks’ awkward fighting style would perplex Tyson, but that wasn’t the case at all. Coming out in his now-iconic black trunks and black shoes with no socks, Tyson was ready to run through Spinks like a hot knife through butter. In 91 seconds, Tyson annihilated speaks, finishing off with a crisp left-right combination to the head, putting down Spinks for good. There were only 10 punches landed between the two boxers, and eight of them were from Tyson. The round was named Round of the Year in 1988 by Ring Magazine. If the world didn’t know already, Tyson solidified himself as the Baddest Man on the Planet and the authentic heavyweight champ of the world.

Date: June 27, 1988

Winner: Mike Tyson (KO)

Title: Once and For All

11. Riddick Bowe vs. Evander Holyfield

After scrapping the Tyson fight after Iron Mike’s incarceration, Evander Holyfield looked to then-undefeated Riddick Bowe. Holyfield had his hands full with Bowe who was the bigger, younger, and stronger fighter. Landing 53% of his shots, Bowe pounded away at Holyfield. However, Holyfield showed plenty of heart and initiated an onslaught of fiery fists, but it wasn’t enough to put Bowe away. The fight won both The Ring magazine’s Fight of the Year and Round of the Year for a brutal round 10 that saw both bulldogs scrap hard. They didn’t initiate much defense, throwing bombs for most of the fight like monsters in kill mode much to the enjoyment of fans across the globe.

Date: November 13, 1992

Winner: Riddick Bowe (split decision)

Title: n/a

12. Julio Cesar Chavez vs. Pernell Whitaker

Simply dubbed “The Fight,” the contest between Julio Cesar Chavez and Pernell Whitaker was a display of boxing tenacity and slick defense. In two rounds, “Sweet Pea” Whitaker configured his defensive skills to counter Chavez’s aggressive offense. Working his beautiful southpaw jab, Whitaker punched Chavez clean whenever the Mexican icon tried to work his menacing left hook. Although many believed Whitaker took the fight, it ended up being scored a majority draw. Sports Illustrated featured a cover titled “Robbed!” to voice the opinion of the masses. Nevertheless, it was an amazing display of the sweet science.

Date: September 10, 1993

Winner: majority draw

Title: The Fight

13. Erik Morales vs. Marco Antonio Barrera

The first Erik Morales vs. Marco Antonio Barrera fight sparked a tremendous rivalry between two highly-skilled leather-fisted assassins. Televised on HBO’s Boxing After Dark program, this PPV-caliber fight didn’t cost anything extra for bringing audiences one of the best matches in history. Once the two men met in the center of the ring they exploded with haymakers and the action didn’t stop until the bell rang in the last round. For all the fists flying about, the only knockdown was delivered by Barrera, although Morales took the W. The controversial split decision led to two more bouts, making a boxing trilogy for the ages.

Date: February 19, 2000

Winner: Erik Morales (split decision)

Title: n/a

14. Micky Ward vs. Arturo Gatti

An all-out war is the only way you can describe fights between Mick Ward and Arturo Gatti. In their first match in what would be a trilogy, they left it all on the floor, as each round was a true slugfest. It’s as if both of them watched the original Rocky film before the match and decided to throw defense out of the window, trading blows nonstop. They threw and ate some ferocious punches, leaving the fight bloodied and bruised. Ward ended up winning by majority decision, but the true winners were the fans in attendance that night.

Date: May 18, 2002

Winner: Micky Ward (majority decision)

Title: Ward v. Gatti I

15. Floyd Mayweather Jr. vs. Manny Pacquiao

As early as 2009, Floyd Mayweather Jr. and Manny Pacquiao were rumored to have a super fight. It took them six years to finally agree on a deal, but it was well worth the wait, at least financially, sine the fight generated $410 million, making it the highest-grossing PPV in history. Granted, it wasn’t the best fight in the world, as the build-up to the match was more exciting. Pacquiao had his moments, and Mayweather initiated his airtight defense with precision, not allowing Pacquiao any clean punches. Money fought a safe fight against Pac-Man, showcasing his boxing IQ to diffuse the Filipino star’s aggression and speed.

Date: May 2, 2015

Winner: Floyd Mayweather Jr. (unanimous decision)

Title: Fight of the Century

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