From Prince Naseem to Anthony Joshua: The nights when British boxing’s brightest hopes came undone

Itauma began his journey to superstardom in 2023 when he turned professional at just 18 years old as a dominant amateur world champion and announced that he planned to beat Mike Tyson’s record - becoming the youngest heavyweight world champion ever. 

After blowing past seven opponents in his first year, the hype train picked up a full head of steam, and before he knew it, Itauma was being compared to Tyson Fury , Anthony Joshua and Oleksandr Usyk .

This fight against Whyte is the biggest challenge Itauma has had to face but there have been times where even our brightest prospects have tripped up on a night like this - succumbing to the hype and pressure. 

Here’s a look back at the nights when some of Britain’s greats came uncharacteristically undone.

Amir Khan vs Breidis Prescott 

On a night that was meant to showcase the rise of a future world champion, British boxing was left stunned as Amir Khan, then an unbeaten Olympic silver medalist and national star, was dismantled in just 54 seconds by Colombian puncher Breidis Prescott in Manchester.

Khan, 17-0 at the time and widely expected to cruise past his relatively unknown opponent, was floored twice in quick succession by Prescott's explosive power. A right hand-left hook combination dropped Khan early, and although he bravely returned to his feet, he never recovered. 

A follow-up barrage forced the referee to wave it off, handing Khan a devastating first-round knockout loss - his first as a professional.

It was a demonstration of boxing’s unpredictability and an exposé of Khan’s defensive frailties. The loss temporarily derailed his momentum and cast doubt on his potential. However, it became a turning point. Khan soon relocated to the U.S., teamed up with trainer Freddie Roach, moved up in weight, and went on to capture a world title at light-welterweight.

Naseem Hamed vs Marco Antonio Barrera 

JOHN GURZINSKI/AFP via Getty Images

By 2001, Naseem Hamed had built a reputation as one of British boxing’s most flamboyant and explosive stars.

He was an unbeaten world champion with knockout power and unmatched showmanship. But when he stepped into the ring against Marco Antonio Barrera in Las Vegas, it was the night Hamed’s aura of invincibility was shattered.

Barrera, often called a brawler, surprised everyone by outboxing Hamed over 12 disciplined rounds. He nullified Hamed’s power with sharp counters, smart footwork, and clinical control of the ring. Barrera, unafraid, even slammed him into the ring post at one point.

What many forget about Hamed-Barrera is that it was a much-closer fight than is often considered: Barrera won by three points on two scorecards, and five on the other.

But what became apparent is that Hamed could be challenged. And when he was, he did not like it. In the ring that night, he looked confused, frustrated, and short of answers. 

While Hamed never officially retired that night, he fought only once more. The loss exposed the limits of his unorthodox style when faced with elite technical opposition.

• Read next |  ​ Joseph Parker's promoter teases world title fight – but not against Usyk

James DeGale vs George Groves

Julian Finney/Getty Images

Few domestic showdowns had as much needle as this one between former amateur teammates turned bitter rivals, both were unbeaten, but it was DeGale—an Olympic gold medallist and rising star who entered the fight a man destined for greatness.

Such was the genuine hatred between the two that, as amateurs, they were kept separate in the gym, told to train at different times.

Held at London’s O2 Arena, the bout was a close, tactical affair rather than the war many expected. Groves boxed smartly off the back foot, using movement and timing to frustrate DeGale, who struggled to land clean shots. Despite DeGale’s claims of superiority in the build-up, it was Groves who got the nod via majority decision, handing DeGale his first professional loss.

The defeat was a reality check for DeGale, whose confidence had bordered on arrogance in the lead-up. DeGale went on to become a world champion and will be remembered as a great of British boxing, but it was a night when a British prospect's hype met a harsh reality.

Anthony Joshua vs Andy Ruiz Jr 

(Getty Images)

Madison Square Garden was meant to be Anthony Joshua’s grand U.S. debut—a showcase of the British heavyweight champion’s power and global star potential. Instead, it became the scene of one of boxing’s greatest upsets.

Late replacement Andy Ruiz Jr, mocked by many for his unassuming physique, tore up the script. The portly fighter had lost a majority decision to Joseph Parker in New Zealand a few fights before, yet it seemed that the Joshua camp were taking him too lightly in the runup.

After being dropped in the third round, Ruiz responded with shocking hand speed and relentless pressure, dropping Joshua four times en route to a stunning seventh-round TKO. It was a fight that mixed brute force and strength with old-school boxing skills - and it was the boxing skills that won.

The loss did not just hand Joshua his first professional defeat - questions over his chin, stamina, and composure under fire flooded in. British fans watched in disbelief as their heavyweight hero was unseated by a man no one thought would win.

Though Joshua would regain his belts in the rematch, that first night in New York was a brutal reminder that even the biggest stars can come undone when they least expect it.

• Read next |  Dillian Whyte's biggest weapon that Moses Itauma must watch out for

David Haye vs Carl Thompson, 2004

Early in his career, long before moved up to heavyweight, 'The Hayemaker' was making short work of every cruiserweight put in front of him. 

After debuting against well-known journeyman Tony Booth in 2002, Haye stopped every single opponent, usually within a few rounds, for the next year-and-a-half.

A three-round win over former world champion Arthur Williams put Haye in line for the lightly regarded IBO cruiserweight title against reigning champion Carl Thompson.

Haye, as he was used to, came out blasting in the first round, but found that Thompson - who had fought and stopped Chris Eubank Sr - unwilling or unable to wilt. The veteran, then aged 40, took all that Haye threw, waited, and then began to throw back.

Such an approach - bordering on arrogance - was a mistake for Haye. He began to gas within a few rounds. Seeing his chance, Thompson turned up the pressure and eventually dropped Haye, battering him until the fight was stopped.

Watch Itauma vs Whyte live on DAZN

Moses Itauma vs Dillian Whyte is live and exclusive on DAZN PPV this Saturday, August 16. Buy the PPV for a one-off fee or get it for free by purchasing a DAZN annual subscription (exc. US).

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