Oleksandr Usyk, the undisputed heavyweight champion, has battled elite opponents across two weight divisions, including 24 grueling rounds against Tyson Fury. However, in a surprising revelation, the Ukrainian fighter admitted that “The Gypsy King” was not the toughest opponent he has ever faced.
Despite his flawless record—boasting an Olympic gold medal from London 2012 and the undisputed cruiserweight championship before conquering the heavyweight division—Usyk confessed that another fighter gave him his most difficult challenge.
Shockingly, in an interview with talkSPORT Boxing, Oleksandr Usyk revealed that Derek Chisora, not Fury or Joshua, was his toughest opponent. “I think it is Derek. My friend Derek. Hey, Derek, I am coming for you!” Usyk joked before adding, “Derek is a terrible guy, really tough. It’s just hard [fighting] Derek. He was just very difficult.”
This statement stunned many, considering the high-level opposition Usyk has faced throughout his career. His revelation underscores the unique challenge posed by Chisora, a relentless brawler known for his pressure and durability.
Derek Chisora poses for a photo with his team and guests as he celebrates victory following the Heavyweight fight between Derek Chisora and Otto Wallin as part of Derek Chisora v Otto Wallin, The Last Dance card at Co-op Live on February 08, 2025 in Manchester, England. (Photo by Alex Livesey/Getty Images)
Although Usyk secured a unanimous decision victory over Chisora in 2020, many analysts and fans acknowledged that the Briton gave him one of his most physically taxing fights, laying the groundwork for strategies that other heavyweights have attempted against the Ukrainian champion.
Usyk: A legacy of triumph and adversity
Usyk’s career is a testament to his skill and resilience. From his meteoric rise in the cruiserweight division—where he became the undisputed champion—to his dominance in heavyweight, he has consistently proven himself against the best. His move to the premier division saw him defeat top contenders like Chaz Witherspoon and Chisora before dethroning then-unified champion Anthony Joshua in back-to-back victories.
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After dispatching mandatory challenger Daniel Dubois in a controversial bout, Usyk took on Fury in a historic showdown for the undisputed heavyweight title. Emerging victorious once again, Usyk cemented his legacy as one of the rare fighters to hold undisputed status in two weight classes—joining legends such as Terence Crawford and Naoya Inoue.
A potential Usyk vs. Chisora rematch?
Chisora, who recently earned his 49th career victory by defeating Otto Wallin, has expressed interest in one final fight before retirement. While a rematch with Usyk remains unlikely, the Ukrainian champion’s unexpected admission adds another layer to their shared history—one that continues to intrigue boxing fans worldwide.
