Our Thoughts on Boxing greatest trilogies

The nature of Boxing means that a fighter will often face an opponent more than once in their career. Rematches always add a level of intrigue and when this is taken to a third fight, the narratives become even more compelling, creating some of the best fights in boxing.

Every fan will have their own favourite boxers and matches, which always produce endless debate about the best boxers, best fights and best boxing trilogies. Whether its old adversaries refusing to back down, a fallen rival looking to avenge a loss or the biggest two in the division slugging it out, each trilogy has its own story to tell. 

So how does Tyson Fury v Dereck Chisora (III) compare?

With tickets for Tyson Fury and Dereck Chisora now available, will this go down in history as one of the greatest boxing trilogies? Well, no…but it gives us an excuse to look back on five of our favourite three fight match ups.

Of course these things are subjective so its up to you if these are the greatest boxing trilogies, we list them in no particular order and make no apologies for the ten (plus) more we couldn’t include!

Saul ‘Canelo’ Alvarez v Gennady Golovkin

Many trilogies start with a draw and so it was the case for Canelo v GGG, in a controversial first fight in 2017. Golovkin was unbeaten coming into the match and looked to be the winner of a tight bout on many scorecards (out-landing Alvarez in 10 of 12 rounds), but the third judge gave the fight to Alvarez by a wide margin, resulting in a draw and causing uproar.

Talks for the rematch began immediately and it took place a year later, which would have been sooner but Canelo was banned for 6 months for failing a drug test. It was another tight fight, this time scored in favour of Canelo. While the fight was superb (and voted fight of the year in many places) it was again not without controversy, as many media outlets had again scored in favour of GGG. The magnanimous Kazahk took it well, but resentment simmered for years, until they could agree the third fight in 2022. Sadly for GGG, age had somewhat caught up with him and Alvarez finally put the discussion to bed, beating his old rival in a unanimous decision.

Canelo v GGG
Fury v Wilder
Tyson Fury v Deontay Wilder

So while the next Tyson Fury fight (against Chisora) may not be on this list, the Gypsy King has been involved in the most thrilling trilogy of recent years, against American slugger Deontay Wilder. Having promised to fight each other in 2014 and goading each other in 2016, the first fight finally game to fruition in 2018 (after Fury’s long absence from the sport).

Wilder was a strong favourite for a fight which many scored Fury as winning, but ultimately ended in a draw. It will be best remembered for the 12th round, when Wilder looked to have knocked the Brit out, only for Fury to somehow beat the count. It was the first Tyson Fury fight he had been put down in.

With both fighters feeling they had won the first fight, a rematch was quickly arranged, this time Fury emerging victorious with a technical knockout in the seventh round. It was all set up then for the trilogy, which came to fruition in October 2021. If the previous two bouts were excellent, this Fury Wilder fight was even better, in a ding dong battle between the pair. Back and forth it went, Wilder down in the 3rd, Fury in the 4th and looking in trouble – before he re-asserted himself and ultimately finished Wilder off in the 11th round. Wilder didn’t take the defeat well, but came away proving he was a warrior, while Fury cemented his legacy as one of the best in the division.

Manny Pacquiao v Erik Morales

Two men who know their way around a boxing legacy and then some. Both fighters could legitimately have another trilogy in here (Pacquiao against Marquez, Morales against Barrera) but this one is chosen for the sheer explosiveness of the fights and the speed in which they all took place (inside 18 months of each other).

Pacquiao was a fighter on the rise as he faced the three divisional Champ Morales in March 2005, but it was the Mexican who showed his class with a unanimous decision (turning southpaw in the 12th round just for bants). As he showed many times in his career, Pacquaio didn’t let a defeat stop him from coming back for more, which he did just under a year later. This time he was the dominant force, stopping Morales for the first time in his career via a TKO. 

A third fight was quickly arranged and they would face each other again before the year was out. With the score tied at 1-1, a third round knockout for Pacquiao emphatically sealed the trilogy. Morales couldn’t believe he lost the fight, sitting speechless in his corner for 5 minutes afterwards, and his career was on the decline from there. Meanwhile the little Filipino continued his upward trajectory with a series of explosive bouts.

Pacquiao Morales
holyfield v Bowe
Evander Holyfield v Riddick Bowe

A true slugfest of a trilogy, with some epic fights and a little bit of farce (of course, this is boxing). In 1992 Holyfield was the undisputed heavyweight champion. Riddick Bowe was an up and coming fighter, who had earned his shot and the title and many felt was the first real threat Holyfield had faced to his title, after previous uninspiring defences.

Bowe was bigger, stronger and quicker than Holyfield. He dominated the fight, nearly knocked him out and took his title by a unanimous decision, in a match considered by many as one of the greatest heavyweight fights.

By the time they fought again a year later, Bowe had forfeited his WBC title after refusing to face Lennox Lewis, but the other titles were on the line. Both men traded punches from start to finish in another huge battle, which was overshadowed by the bizarre ‘Fan Man’ incident of a parachutist crashing into the ring during Round 7. He was knocked out, the fight was delayed for 21 minutes and Holyfield eventually won it on points.

The third fight was concluded 2 years later in perhaps the most brutal of the trilogy. Bowe was knocked down for the first time in his career but came back to put down Holyfield several times and stop him in the 8th round – the first time he had been beaten by knockout. It was an apt way to finish one of the biggest punching trilogies. Interestingly, Holyfield would recover to win the heavyweight title for a second time (and face Mike Tyson twice) while Bowe’s career somewhat fizzled out.

Muhammad Ali v Joe Frazier

Probably the most famous and greatest boxing trilogy of all time, featuring two of boxings biggest names, this one is hard to argue with. Their first fight was billed as ‘Fight of the Century’, so it had a lot to live up to and actually did. It was the first time two undefeated heavyweight title boxers had come together, in a country polarised by the Viernam war. Tickets were so in demand that Frank Sinatra couldn’t get ringside, so worked for Life Magazine as a photographer instead. The fight went the distance, with Frazier taking a unanimous decision after putting Ali down in the last round.

Their second fight wouldn’t take place until 3 years later, when many felt that Ali was on the way down and Frazier had been overturned as heavyweight champion by George Foreman. With this, and the fact it wasn’t a title fight in mind, it was the least interesting of the three bouts, but Ali came away with a close points victory. Ali would go on to stun George Foreman in the Rumble in the Jungle and the third fight against Frazier was arranged, as the Thrilla in Manila.

Oddly started at 10am local time (to accommodate international TV viewing) and oppressively hot, it was a brutal fight, with both men taking out their years of hatred on each other. Frazier struggled with his eyesight, Ali was quoted as saying it was ‘the closest he had come to dying’ and both men took a multitude of punches. It was finished as the end of the 14th round as Frazier’s trainer threw in the towel, knowing his man could no longer see. It came out later on that Ali was close to quitting himself, but just managed to outstay his opponent and secure his legacy.

Frazier v Ali

So that’s five great boxing trilogies, what did we miss? And where would the Tyson Fury fight against Dereck Chisora fight rank? (be nice…)