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Home Sports

Fifty and Out for the Forty-Somethings

by Theinsightpost
March 30, 2026
in Sports
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Fifty and Out for the Forty-Somethings

Is it a final ‘War’ for Derek Chisora, and will Deontay Wilder come out swinging once more? The two boxing veterans square off at the 02 Arena on Saturday, 4th April, looking to make one more iconic statement in their twilight years.  Between them, a century of fights awaits…

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Recent Form…

Chisora has already been vocal in outlining that it will be ’50 and out’ for him, and he comes into this last dance in great form.  His last three bouts have all gone the full distance, in which he has demonstrated his durability, winning by decision each time.  ‘Del-Boy’ – as he is fondly known – has never ducked a fight.  He’s been honest in admitting that he is fuelled by big paydays.  He has regularly faced off against the very best opponents in high-profile clashes, stating in 2019 that: “I’m not the guy interested in the belts anymore… I’m the money-weight fighter of the division”. 

He always gets the crowd onside, especially in London.  And although he’s had 13 defeats in his 49 matches, he’s only been stopped on four occasions.  At 42 years old, Chisora is clearly picking his fights more sparingly now. His last three victories mean he now has 36 W’s on his record, but his last fight was more than a year ago.

Otto Wallin was beaten by unanimous decision in February 2025, so will ‘ring rust’ catch up with him or does ‘War Chisora’ remain a stubbornly immovable object?

Wilder, meanwhile, has been known as the hardest puncher of them all for his entire career.  Until 2020, he could boast an unbeaten record, but recent years have been harsh on the ‘Alabama Slammer’.  He has been beaten in FOUR of his last SIX fights, including being stopped on three occasions. 

The gruelling trilogy with Tyson Fury will go down in folklore and, in some ways, arguably enhanced his reputation as a boxer.  After all, he was invincible in his first 43 contests – which included 41 knockouts and a draw with Fury.  Successive defeats to Fury (in 2020 and 2021) were broken up with a first-round knockout win against Robert Helenius in 2022 – but it was back-to-back defeats once more to Joseph Parker and Zhilei Zhang in Saudi Arabia.  The Zhang defeat was especially brutal – an untidy KO with him turning his back to the Chinese giant before being felled.

He did stop Tyrell Herndon in his last match-up in June last year, but is his once-great power now waning?

Career Highlights…

Chisora:

Chisora’s career has been a long and action-packed one.  It has been defined by his toughness and frequent ‘marquee’ fights.  He turned professional in 2007 and won the British Heavyweight title by beating Danny Williams at Upton Park.

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He is known for his relentless ‘pressure style’ and has shown he can absorb a lot of punishment from opponents.  He has shared the ring with all the greats.  Tyson Fury on three occasions.  The ‘Gypsy King’ is one of the few men who has been able to stop Chisora – doing so on two of those occasions.  The final match between the two, as recent as 2022, was clearly a mismatch, but it was remembered as much for the post-match events with the two men sharing burgers in the dressing room afterwards.  A show of mutual respect and evidence of Chisora’s great character.

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He challenged Vitali Klitschko for World honours in 2012.  The fight went the distance, but he lost via a unanimous decision.  He would also go the full distance with arguably the ‘greatest of them all’ Oleksandr Usyk in 2020.  The following year, in 2021, he fought Joseph Parker twice, going 12 rounds both times and losing by decision.

In the Usyk fight, Chisora caused him significant problems, particularly early on, by using aggressive, high-pressure tactics to crowd the Ukrainian. Chisora’s size and physical “bullying” forced a vulnerable-looking Usyk onto the back foot, causing some to view it as one of Usyk’s hardest heavyweight tests to date.  For a while afterwards, it was even suggested that this was the ‘blueprint’ to be able to succeed against the unbeaten Ukrainian. But no one has been able to execute the plan successfully against the classy Champion.

Derek Chisora has thrived off being the ‘underdog’ throughout his career.  He claimed a huge scalp when he beat the dangerous Joe Joyce in 2024 – flooring his opponent in a thrilling performance.  In his last outing, he was dominant against Otto Wallin, winning via a unanimous decision.  This was a superb win against an opponent that also went the distance with Tyson Fury and had only been stopped by Anthony Joshua.

Wilder:

Deontay Wilder’s career has been packed full of eye-catching knockouts, including an incredible 20 of them in the very first round.  His knock-out to win ratio is 97.7% (42 KOs in his 43 wins).

He won a bronze medal at the 2008 Olympics – turning pro shortly after.  He quickly built up an unbeaten record that lasted 12 years – and saw him crowned WBC Champion in 2015 after overcoming Bermane Stiverne.  His multiple knockout victories earned him the reputation as one of boxing’s hardest ever punches. 

Deontay Wilder’s best victory is widely considered to be his seventh-round knockout of Luis Ortiz in their November 2019 rematch. While trailing on all of the scorecards, Wilder demonstrated patience and elite power, solidifying his reputation as a devastating puncher against a top-rated, experienced southpaw in Ortiz.

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However, questions remained about the quality of the opponent he was facing.

This all changed during his own iconic trilogy with Tyson Fury.  Like Chisora, he failed to beat Fury – but did claim a draw in the first bout.  Across the three meetings, he knocked Fury down on four separate occasions.

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Wilder’s recent victory over Tyrrell Herndon was his first since October 2022.  He dropped his opponent on two occasions before it was waved off by the Referee in the ninth round.  Whilst it was a comfortable victory, it was far from the vintage ‘Bronze Bomber’ of previous years.

It was a low-key victory for a man once surrounded by all the glitz and the glamour, but he feels it could be a ‘fresh start’ for him, even at the age of 39 (which he was at the time).

He stated: “I’ve been laid off for a long time, getting myself back together, repairing myself emotionally. It is just nice to be back in the ring. This is a new beginning for me.”

It has long been said that ‘Life begins at 40.’  For Wilder, is this the dawning of a new era in his career?  After all, he’s said he won’t be retiring anytime soon.

The verdict…

Ex-middleweight Champion-turned pundit Carl Froch has said he can only see one winner.  He feels Wilder has lost his ‘fear factor’ and stated, “He doesn’t generate power anymore for me. He’s not a big puncher anymore.”

Froch went on to predict that Chisora will be ‘relentless’ as usual, and his verdict was: “Worst-case scenario, Chisora wins it on points.”

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From a spectator’s perspective, they will be hoping for an entertaining clash and would love to see the fireworks of a KO.

The longer the fight goes, the scrappier it will become.  It will not be for the technical boxing purists if it goes deep.

For me, if Wilder’s power remains, then he wins it via KO in the early rounds.  If not, I see Chisora doing what he’s done so well in recent fights – as he saps the energy of his opponent and remains strong in the later rounds to take the decision.

My Prediction: Wilder early KO (Round 2-5), or Chisora UD.

What next?

Derek’s ‘War’ is over, whatever happens, according to him.  But will he have another ‘itch to scratch’ if he manages to complete a fourth victory in a row?

Wilder has come through some personal issues in recent years – and has claimed he’s still in his “prime” even now.  He has even suggested he could fight until he’s 50.  But if so, would anyone actually want to see that?

The stage is set. The 50th match for both. Chisora,42, v.s Wilder, 40, on Saturday 4th April, at The O2 Arena, London.

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Fifty and Out for the Forty-Somethings

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