Potential opponents for Derek Chisora’s farewell fight – from Oleksandr Usyk to Anthony Joshua

Derek Chisora’s next bout will be the 50th of a long career, and if he stays true to his word, it will also be his final fight.

Shortly after his most recent bout, a win over Otto Wallin, Chisora took a novel approach to matchmaking, presenting three posters to the crowd and asking them to choose his next opponent.

The options he presented included Daniel Dubois, Anthony Joshua, and Oleksandr Usyk, with the Co-op Live crowd seeming to prefer either Joshua or Usyk.

Unfortunately for Chisora, organising a fight isn’t as simple as gauging public opinion – but who could he actually face before hanging up his gloves?

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Chisora’s victory over Wallin in February saw the British veteran become the International Boxing Federation's mandatory challenger at heavyweight, although the title picture with the IBF is somewhat murky.

That is complicated by the fact the IBF have ordered an eliminator between Frank Sanchez and Frank Ajagba, suggesting that Chisora could be bumped out of the queue.

At the time of Chisora’s win Dubois was the IBF champion, but he has since lost his strap to undisputed heavyweight king Usyk.

One of the three options listed by Chisora after his most recent fight, Usyk also implied that he was open to facing the Brit in the aftermath of his win over Dubois.

Usyk stated: “Maybe it’s Tyson Fury. Maybe we have three options – Derek Chisora, and Anthony Joshua. Maybe Joseph Parker. I cannot say now.”

The pair first faced each other in 2020, where Usyk took a unanimous decision win over Chisora. Two of the judges had it very tight at 115-113 in favour of the Ukrainian, but five years later many would expect Usyk to be a clear winner.

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A chance meeting between Chisora and Martin Bakole on IFL TV produced some very amusing quotes, with the former having a go at the latter for piling on the pounds in between fights.

Having carved out a niche as the heavyweight division’s boogeyman, Bakole’s stock has dropped slightly after a knockout loss to Parker, followed by a subdued draw against Ajagba.

Chisora is another vanquished Parker foe, and a contest between a heavy-hitting puncher like Bakole and a fighter who doesn’t know when to quit in could produce a thriller.

A major sticking point could be the choice of venue. In that aforementioned interview, Bakole said he wanted a big stadium fight in the UK, whilst Chisora has frequently spoke about his final fight being staged in Africa.

Born in Zimbabwe, Chisora moved to the UK with his family as a teenager, whilst Bakole, of the Democratic Republic of Congo, has relocated to Scotland to help his boxing career.

A return to Africa for both fighters could give Chisora the romantic farewell he is after.

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Whilst not quite a prospect at the age of 30, Fabio Wardley has emerged as one of the faces of Britain’s next generation of heavyweights.

He claimed the interim WBA title at the start of June to cement his position as a top contender, but with all four belts in the possession of one man, it is a waiting game for Wardley.

A fight with Chisora poses enough threat to make things interesting and attract a crowd, with both fighters proving they are strong ticketsellers. For Chisora, a fight with Wardley could represent a changing of the guard. If he wins, he goes out on a high, while there would be no shame in losing to a man 11 years his junior.

For Wardley, not only would it be a big name on the CV but a step up in opposition, both in terms of quality and experience.

Chisora’s willingness to step into the ring with pretty much anyone has seen him pick up a few losses, but Wardley has not faced many seasoned veterans in the first 20 fights of his career so this could offer him a new challenge.

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Forty-nine fights into a professional career, you start to run out of opponents on a similar level to your own. Chisora is prone to getting into the ring with the same fighter multiple times, as evidenced by his losing record in a trilogy of bouts with Tyson Fury.

When it comes to top level British fighters, there are not many that Chisora is yet to come to blows with. Chisora's longevity means he has shared the ring with names such as David Haye and Danny Williams, whilst he is well acquainted with Fury, Dillian Whyte, and Joe Joyce, prominent fighters of his own generation.

One fighter he has not fought is Anthony Joshua, who happened to come through the same Finchley ABC gym as Chisora.

Chisora frequently refers to Joshua as his brother, but the Zimbabwean-born boxer has called out the younger man before. With Joshua rebuilding following a shock loss to Daniel Dubois in September 2024 and elbow surgery earlier this year, this all-British heavyweight clash could finally be made.

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In an ideal world, Chisora would be fighting Dubois for the IBF heavyweight title this year. However, the option to unify all four belts in boxing’s glamour division came up for Dubois, and no heavyweight would turn that down.

Dubois suffered another knockout loss to Usyk, demoting him back to contender status in the heavyweight division. At only 27, Dubois has plenty of time to get back into the mix, but appropriate opponents will be hard to come by.

Chisora could then present the perfect challenge. An experienced fighter capable of asking questions of anyone, Dubois’ credentials – especially the debate over a tendency to ‘quit’ - would truly be tested.

Dubois was another of the three names listed by Chisora after his victory over Wallin, suggesting he is more than open to the fight.

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