Heavyweight veteran Derek Chisora is actively angling for a high-profile slot on the upcoming Tyson Fury versus Anthony Joshua undercard, setting his sights firmly on securing a long-awaited rematch against an old domestic rival.
The 42-year-old Londoner is currently looking to bounce back following a hard-fought split decision defeat to former WBC champion Deontay Wilder in April. That chaotic 12-round affair saw Chisora endure two knockdowns, yet it once again highlighted the enduring durability and relentless fighting spirit that have defined the latter stages of his storied professional career.
Prior to his setback against Wilder, Chisora had enjoyed a notable resurgence in form. A punishing 10th-round stoppage defeat to Tyson Fury in December 2022 had initially led many observers to question whether the veteran heavyweight had reached the end of the road. Back then, that bout marked a rather pointless trilogy encounter, given that Chisora had already lost his previous two meetings with "The Gypsy King" in relatively convincing fashion.
However, rather than fading away into retirement, Chisora responded with a surprising and impressive purple patch. He strung together a succession of back-to-back victories, securing hard-earned unanimous decision wins over Gerald Washington, former world title challenger Joe Joyce, and formidable German contender Otto Wallin. Those victories proved that "Del Boy" still possessed enough tactical awareness, stamina, and grit to trouble world-class heavyweights.
Now, Chisora is turning his attention toward an opponent who represents a far more winnable and historically charged contest: Dillian Whyte. The two British heavyweights share a deep and deeply competitive professional history that dates back nearly a decade. Their first encounter took place in December 2016, a brutal and enthralling war of attrition that ultimately saw Whyte edge a contentious split decision. Despite the controversial nature of the verdict, the fight was universally praised as one of the finest domestic heavyweight battles of the modern era.
The pair squared off again two years later in a similarly dramatic rematch. In another fiercely contested war, Whyte managed to solve the puzzle in the championship rounds, landing a devastating left hook that produced a dramatic 11th-round knockout. That victory cemented Whyte’s status near the summit of the division at the time, while leaving Chisora with a lingering sense of unfinished business.
Looking to reignite their fierce rivalry and settle the score once and for all, Chisora has taken to social media to campaign for a third encounter. The veteran heavyweight has called for the trilogy bout to take place at Cardiff’s Principality Stadium on December 11, strategically positioning himself for a spot on the much-discussed Fury-Joshua undercard. To amplify his campaign, Chisora shared a mock-up trilogy fight poster across his digital platforms, drawing immediate attention from boxing fans and media outlets alike.
Whether this ambitious matchup will actually materialize remains to be seen, as the logistics of big-card boxing promotions and sanctioning bodies often present unpredictable hurdles. Yet, if the fight were to be successfully booked, many pundits and boxing followers would likely give Chisora a significantly greater chance of emerging victorious this time around compared to their previous outings.
That assessment is largely driven by the current trajectory of Dillian Whyte’s career. Whyte has been inactive since suffering an emphatic first-round stoppage defeat to rising heavyweight star Moses Itauma back in August 2025. That abrupt loss led many in the boxing community to express concern that the once-feared puncher now looks a mere shell of his former self, having absorbed considerable punishment over the course of his professional journey.
While Whyte has not yet officially announced his retirement from the sport, the 38-year-old is surely approaching the final chapter of his career, with few viable pathways remaining to another world title opportunity. Similarly, Chisora acknowledges that he is likely only one or two fights short of hanging up the gloves for good, making a final high-stakes domestic showdown with his old adversary an appealing and lucrative finale for both men. As negotiations and rumors surrounding the Fury and Joshua event continue to develop, Chisora’s persistent callout keeps the prospect of this heavyweight trilogy firmly in the public eye.
