Top 12 Greatest Trilogy Fights in Boxing History

Top 12 Greatest Trilogy Fights in Boxing History

The human stories are what makes boxing so exciting, and heated rivalries are what make fans invested in a fight. The deeper the story, the bigger the interest. And if two boxers have to fight three times to determine who is the better man, you can bet their styles are tailor-made for each other.

In this blog, we revisit 12 of the best trilogy fights in boxing to this day. Make sure not to skip any because I can assure you that some of the stories outshine Hollywood scripts. 

12. Roberto Duran vs Esteban de Jesus

Roberto Duran vs Esteban de Jesus - boxing trilogy
Roberto Duran vs Esteban de Jesus Bettmann / Contributor

Fight results:

  1. November 17, 1972 – Unanimous decision win for de Jesus
  2. March 16, 1974 – KO win for Duran
  3. Jan 21, 1978 – KO win for Duran

We start with a heated rivalry between two talented Latin American boxers. Many Latin American countries place great national pride in their boxing heroes, and clashes in the ring between two countries are especially fierce. This was the case with Panamian Roberto Duran and Esteban De Jesus from Puerto Rico.

Duran was an undefeated lightweight champion, but instead of defending his title, he decided to take a few tune-up fights first. Esteban De Jesus provided a great ‘victim’, as the Latin rivalry would be entertaining for the fans in New York. But things did not go according to plan, and 30 seconds into the fight, Duran’s back was on the canvas for the first time in his career. He got back up quickly but never fully recovered and after the 10 rounds in this non-title fight, all 3 judges rightfully awarded De Jesus the win. Duran suffered his first professional loss, and a new rivalry was born.

Ready for revenge

Two years later both men were ready to go again, and this time Duran’s belt was on the line in his home country. While the start was repeated and Duran was knocked down in the opening round, the rest of the fight looked nothing like the first. Roberto brutalized the Puerto Rican until the fight was mercifully stopped in the 11th round by the referee.

Fans are not only dissatisfied with splits, but both Duran and De Jesus held lightweight world titles in 1978, making their third clash even more anticipated. This time Duran was careful early on and switched gears when the time was right, never letting off the pressure. The end came in the 12th, with Duran winning the rivalry and proving he is the one and only lightweight champion.

11. RomanChocolatitio’ Gonzalez vs Juan Estrada 

Roman ‘Chocolatitio’ Gonzalez vs Juan Estrada - boxing trilogy
Estrada vs Chocolatitio 2 – Credit: Getty

Fight results:

  1. November 17, 2012 – Unanimous decision win for Gonzalez
  2. March 13, 2021 – Split decision win for Estrada
  3. December 3, 2022 – Majority decision win for Estrada

Despite some valid concerns regarding the state of modern boxing, we cannot complain about a lack of magnificent fights, including some epic trilogy fights in this era. Three times Roman Gonzalez and Juan Estrada went to war, resulting in one of the best rivalries in the lower-weight divisions.

The first meeting in 2012 became an instant classic despite being contested between two 108-pounders not known in the mainstream at the time. Cholocatito won the slugfest with a unanimous decision and retained his WBA light flyweight belt.

Two weight classes and nearly 10 years after the first fight, Chocolatito and Estrada met again, this time in very different positions in their careers. Now both men were flyweight champions, and despite the difference in age, they managed to top all expectations and have an even better fight than the first one.

The pair set a new record for the 115-pound division, throwing a combined total of 2529 punches. Gonzalez appeared to be the winner, but two of the judges saw the fight for Estrada, who unified the WBA and WBC titles with the controversial decision.

The decision ushered in a rematch, which was postponed a few times, but finally happened at the end of 2022. This time ‘El Gallo‘ was the sharper boxer, and his effort in the opening and closing stages sealed the third war and the rivalry in his favor. But with yet another razor-close decision win, this time a majority one, we may yet see a fourth fight between the two future Hall of Famers.

10. Muhammad Ali vs Ken Norton 

Muhammad Ali vs Ken Norton  - boxing trilogy
Ali vs Norton 2

Fight results:

  1. March 31, 1973 – Split decision win for Norton
  2. September 10, 1973 – Split decision win for Ali
  3. September 28, 1976 – Unanimous decision win for Ali

Muhammad Ali would not be the greatest without his iconic rivalries. Ken Norton was supposed to be run over by Ali. But all three of their fights were very closely fought. The big upset came in the first bout in 1973. Norton had a solid 29-1 record at the time but lacked proper recognition, and no one expected him to give Ali one of the most challenging fights of his career, but this is exactly what happened. Ali entered the ring in less than ideal condition and suffered a broken jaw, dubbing the fight “The Battle of Broken Jaw.” Norton got the split decision win and rose to fame.

The upset was so big that Ali demanded an immediate rematch, which, if nothing else, proved the first result was not a fluke. The former champion eked out a decision with a late effort, but the fight was anything but easy for him.

The third meeting featured Ali as the heavyweight champion and Norton as the challenger, and it was the hottest heavyweight fight possible at the time. The fight was very competitive, but Ali was showing his age, and it was clear he was near the end of his career.

The cross guard and counter-striking abilities of Norton again gave him big problems. But the judges gave Ali the win, but even he admitted after the fight that he thought Norton was the real winner.

9. ‘Sugar’ Ray Leonard vs Roberto Duran

'Sugar' Ray Leonard vs Roberto Duran - boxing trilogy
Duran vs Leonard 2 – Credit: Getty

Fight results:

  1. June 20, 1980- Unanimous decision win for Duran
  2. November 25, 1980- TKO win for Leonard
  3. December 7, 1989- Unanimous decision win for Leonard

The Brawl in Montreal‘, as the first fight between Ray Leonard and Roberto Duran was billed, was the first super fight of the 1980s. Duran dominated the lightweight division for nearly 7 years, and Sugar Ray Leonard was the undefeated champion at welterweight and the new love of the American boxing audience.

In front 46 000 people Leonard kept his word and stood and traded flurries with Duran for 15 rounds in what remains one of the greatest fights in the history of the sport. Leonard’s tactical decision cost him the championship and the 0 on his record.

In the immediate rematch held in New Orleans, Leonard learned his lesson and danced around Duran for the whole fight. He used his superior movement and speed to pepper with punches and taunt the champion the entire time. The performance was so dominating that it forced the now famous “No Mas” at the end of the eighth round. Duran just turned his back to the referee and said “no more.”

Unlike most other trilogies, the third fight between the two did not bring any real meaning to the rivalry as it happened way after both men were in their prime. Despite the big crowd and expectations, the fight was utterly lackluster, and Leonard won a lopsided decision. But the quality of the first two fights more than made up for the third.

8. Canelo Alvarez vs Gennady Golovkin 

canelo vs golovkin - boxing trilogy

Fight results:

  1. September 16, 2017- A draw
  2. September 15, 2018- Majority decision win for Canelo
  3. 2022 – Unanimous decision win for Canelo

Another recently concluded great trilogy is that of Canelo Alvarez and Gennady Golovkin. The Kazakhstani knockout artist was the long-reigning middleweight king when the biggest star of boxing today, Canelo, came to challenge him for supremacy, as their first fight was billed. The fight in Las Vegas lived up to all expectations of being a “big drama show,” in the words of GGG. In an instant classic where both Golovkin and Canelo had great moments throughout the fight, But it was Golovkin who looked to have won the fight by using his jab and pressure. However, the judges very controversially declared it a split decision draw.

The ending was very disputable, and talks of a rematch immediately started but did not materialize right away because Canelo tested positive for a banned substance, further adding to the controversy.  Exactly a year after the first bout, the rematch was a fact, and while the fight itself was different, the result was still controversial. This time, Canelo was more aggressive and landed more power shots, while GGG was more accurate with the jab. The Mexican star prevailed by a majority decision, which was again received with an uproar as many boxing outlets scored it for Golovkin.

Golovkin made a move up in weight to meet Alvarez for the third and decisive time and challenge him for his undisputed super middleweight title. This time around, the fight was not competitive as the 40-year-old GGG showed his age and, despite not being in real danger at any time, clearly lost the decision.

7. Tyson Fury vs Deontay Wilder

Fury vs Wilder - boxing trilogy

Fight results

  1. December 1, 2018 – A split draw
  2. February 22, 2020 – TKO win for Fury
  3. October 09, 2021 – KO win for Fury

Continuing the great heavyweight tradition of heavyweight boxing rivalries. Tyson Fury and Deontay Wilder brought all eyes back on the heavyweight division with their epic trilogy. The two undefeated Titans squared off for the first time in 2018.

The story of the fights was Fury’s boxing prowess against Wilders’ dynamite right hand. And for most of the fight, boxing was winning until, in the 9th round, Fury was dropped for the first time by a hard right hand.

After getting back in control, Fury ate Wilder’s best punch in the 12th and looked dead on his back. Until somehow he wasn’t, to the bewilderment of the crowd and even his opponent. Fury was back on his feet and ended up pressing the WBC champion to the final bell. The split draw may not have been the technically correct decision, but it was the just one. And the one needed to heat up the rivalry further. (Watch the 12th round below)

In the inevitable rematch, Fury came in heavy and utilized every pound of his weight, quickly bringing the fight to Wilder and sapping his energy. Deontay was thoroughly dominated, and in the 7th, his corner spared him the knockout by throwing in the towel.

Ending in style

The loss was very tough on Wilder, but he used that as fuel, and the final showdown between the two was the real culmination. It looked like Wilder would be finished even earlier this time after falling to the canvas in the third. But he showed what a warrior he is by knocking down Fury twice in the fourth.

The following rounds were filled with pure guts, determination, and gargantuan power by both men until Wilder took his final blow in the 11th round, and the trilogy ended with an exclamation point.

6. Tony Zale vs Rocky Graziano

 Zale vs Garziano - boxing trilogy

Fight results:

  • September 27th, 1946 – A KO win for Zale
  • July 17th, 1947 – TKO win for Graziano
  • June 10, 1946 – KO win for Zale

One of the most iconic trilogies in boxing history is the series of fights between Tony Zale and Rocky Graziano. These two middleweight warriors gave fans three unforgettable battles that are still talked about to this day.

Their first fight took place at Yankee Stadium in New York City in 1946. Zale was the champion and was heavily favored to win, but Graziano had other plans. The fight was an all-out war, with both men trading heavy blows from start to finish. Zale knocked Graziano down in the first round, however, but he would go on to In the sixth round, Graziano knocked Zale down, but the champion managed to get back up and stop Graziano in the sixth round, retaining his title.

Their second fight was even more intense, with both men exchanging knockdowns throughout the fight. Zale managed to knock Graziano down twice in the first round, but somehow Graziano battled back and ultimately stopped Zale in the sixth round to become the middleweight champion.

The third and final fight between Zale and Graziano took place in 1948 and was for the middleweight championship once again. (Luckily clearer footage) This fight was arguably the most dramatic of the three, with Zale dominating and knocking Graziano down in the first. However, Graziano showed incredible heart to stay in the fight, before Zale took him out in the 3rd and final fight to regain his middleweight title.

The Zale vs Graziano trilogy is often cited as one of the greatest in boxing history, with all three fights delivering thrilling action and unforgettable moments.

 5. Floyd Patterson vs Ingemar Johansson

Floyd Patterson vs Ingemar Johansson - boxing trilogy

Fight results:

  1. June 26, 1959 – TKO win for Johansson
  2. June 20, 1960 – KO win for Patterson
  3. October 09, 2021 – KO win for Patterson

Ingemar Johansson became a national hero in Sweden by beating Floyd Patterson for the heavyweight title in 1959. Patterson was knocked down 7 times in the first 3 rounds when the referee decided he saw enough.

The American trained relentlessly and came out like a man possessed in the rematch a year later. Patterson battered Johansson and knocked him out using the Gazelle Hook, with the Swede remaining on the canvas and quivering for 5 minutes.

The rubber match turned the rivalry into an annual event, and the third time around did not disappoint. Patterson tasted the canvas twice looking like the Swede would regain his titles. In the sixth, however, Patterson put Johansson down with two right hands, and the challenger failed to beat the count.

4. Evander Holyfield vs Riddick Bowe

Evander Holyfield vs Riddick Bowe - boxing trilogy

Fight results:

  1. 1992 – Unanimous decision win for Bowe
  2. 1993 – Majority decision win for Holyfield
  3. 1995 – KO win for Bowe

Holyfield vs. Bowe I (Fight of the year 1992) was one of the greatest heavyweight title fights of all time. Holyfield had stormed the heavyweight division from below and was on a string of three successful defenses of his three belts. However, Riddick Bowe proved too much for any boxer at the time, stripping Holyfield of his titles and undefeated record in a barnburner. The smaller Holyfield was hurt in the 9th and dropped in the 11th, but came back swinging, and both men showed incredible determination in that fight.

Part two of the rivalry will always be remembered for the 7th round “Fan Man” incident when a parachutist landed in the ring. Halting the contest for 25 minutes on either side of another tremendous battle. In the end, Evander earned back his title with a majority decision.

By the third clash in 1995, both men were now ex-champions, and Bowe survived a heavy knockdown in the 5th round. only for him to get up and knock out Holyfield two rounds later.

3. Marco Antonio Barrera vs Erik Morales

Marco Antonio Barrera vs Erik Morales - boxing trilogy
Marco Antonio Barrera vs Erik Morales 2 – Credit: (AP Photo/Laura Rauch)

Fight results:

  1. February 19, 2000 – Split Decision win for Morales
  2. June 22, 2002 – Unanimous decision win for Barrera
  3. November 27, 2004 – Majority decision win for Barrera

The rivalry between two Mexican boxers to assume the throne of Julio Cesar Chavez as the country’s boxing icon was always destined to be epic. Barrera and Morales came from very different classes in Mexico and had very different ways in the ring, so their animosity towards each other was not fabricated.

The whole fight showcased the brutal brilliance of boxing. The Ring Magazine named the fight the best of the year 2000. Later that year it was named the best fight of all time. Both men landed around 300 punches on each other, and despite Morales touching the canvas in the 12th. He got the split decision win and a couple of super bantamweights major belts.

In 2001, the two came to blows in a press conference, setting the stage for another clash in the ring. It materialized in 2002. And despite being labeled the most technical fight of the three, heavy punches were flying the whole fight. Barrera was declared the winner by a unanimous decision. But as is usually the case with such evenly-matched fights, this was heavily disputed.

The old foes met for the final time at super featherweight. This time, Barrera started faster and hurt Morales in the second. There were no knockdowns this time, but the heart and skill shown by both warriors made their third meeting the fight of 2004, which was again won by Barrera.

2. Arturo Gatti vs Micky Ward 

Phot credit: Marty Rosengarten

Fight results:

  1. May 18, 2002- Majority decision win for Ward
  2. November 23, 2002- Unanimous decision win for Gatti
  3. June 7, 2003- Unanimous decision win for Gatti

All trilogies are bound to be evenly matched, but none was as brutal and barbaric as the one between Arturo Gatti and Micky Ward that took place in the span of 13 months.

When these two first fought, the idea was that Micky Ward, an aging club fighter with 11 losses, would be picked as a tune-up fight for Arturo Gatti. But instead, the Canadian found himself in the fight of his life, which would define both men and their careers. The bout was all about blood, guts, and pain, and the unlikely winner was Micky Ward.

After being a clear Fight of the Year winner. Fans were salivating for more of the same, and they got it. Though the second fight did not live up to the hype of the first, it was still entertaining, and Gatti won by a unanimous decision. He could have advanced his career to title matches, but he chose to repay the favor by rematching Ward.

The rubber match more than made up for the slower second and was another fight for the year. For 10 rounds, Ward and Gatti battered each other relentlessly. Gatti had to survive a broken hand to claim another decision victory.

Ward and Gatti not only became close friends after the fights, but Ward also ended up coaching Gatti at the end of his career, making the after story possibly even better than the fights themselves.

1. Muhammad Ali vs Joe Frazier

Muhammad Ali vs Joe Frazier Trilogies

Fight results:

  1. March 8, 1971 – Unanimous decision win for Frazier
  2. January 28, 1974 – Unanimous decision win for Ali
  3. October 1, 1975 – TKO win for Ali

If one rivalry transcended not just boxing but sports overall, it would be that between Muhammad Ali and Joe Frazier. The two are forever linked thanks to their timeless trilogy in the ring. The only way we learned what greatness they possessed was because their contrasting styles and personalities brought out that greatness in each other.

The first fight between Ali and Frazier billed as ‘The Fight of the Century’, had to prove who the real champion was. Both were undefeated, and Frazier was holding the belt, that Ali never lost but was stripped of for refusing to fight in Vietnam. In an epic battle capped by an iconic left hook that sent Ali to the canvas with a swollen jaw in the final round, Frazier proved that he is the true champion and avenged Ali’s heavy insults before the fight.

But the rivalry was far from over. Three years later, they met back in the ring, but this time neither man was the champion, and the fight was the least memorable of the three. Ali outboxed Frazier for 12 rounds and got the decision win.

The Thrillia in Manila

A year later, Ali was once again the heavyweight champion of the world, and the inescapable rubber match happened as ‘The Thrilla in Manila‘ The result was one of the most grueling and brutal battles in the sport, where both men went through hell. After 14 rounds of action, Frazier’s coach Eddie Futch did not let him come out of his corner, and Ali was the winner. But he was so exhausted and hurt that he couldn’t even celebrate.  

He could have whupped any fighter in the world, except me. He is great – greater than I thought. He is one hell of a fighter and it was one hell of a fight.

Ali pays tribute to Frazier

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Jamie - Boxing Life

I'm a boxing analyst, amateur boxer, and blogger looking to pass on my boxing experiences and passion to anyone looking to learn or find out more about the sport of boxing. Whether that be gear reviews, fighter analysis, news, training tips, or my own personal journey, I'll be covering it on 'Boxing Life'.

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