Derek Chisora has named the toughest opponent he’s faced in his career. Having debuted back in 2007, the veteran heavyweight boxer has faced many of the division’s best over the last 19 years.
The popular 42-year-old has shared the ring with the likes of Oleksandr Usyk, Vitali Klitschko and David Haye. The Londoner has even squared off with Tyson Fury on three separate occasions.
Never one to back down from a challenge, ‘War’ Chisora is known for his toughness. Despite having a resume packed with top names, he’s only been stopped on four occasions throughout his whole career.
GiveMeSport sat down for an exclusive chat with the former world title challenger to ask him about his storied career. Asked to name his toughest fight, Chisora gave a surprising response.
Derek Chisora’s Toughest Opponent
Snubbing names such as Fury and Usyk, Derek gave the nod to a foe that he emerged victorious against:
“Toughest fight? I’d have to give it to Otto Wallin.”
Chisora beat the Swedish heavyweight via unanimous decision, but was made to work hard for his February 2025 victory in Manchester. In what had been due to be his final fight on UK soil (he later changed his mind on that matter), the Brit went all out to try and dominate from the very first bell.
‘I Was Wrong’ – Derek Chisora Admitted His Error Before Toughest Fight
Fighting on the front foot, Chisora worked hard to deny Wallin the opportunity to get his jab away effectively. The home favourite later admitted that his strategy was to put pressure on his less experienced foe in the hope that he wouldn’t be able to mirror the same workrate.
“I thought he was going to gas out, but he didn’t, and I was wrong,” Chisora said at the time. “It was a firefight.”
As Wallin found his way into the contest, he cut Chisora above his right eye in round five. Although the ringside doctor took a close look at the wound, Derek was allowed to continue and went on to knock the Swede down with a looping right hand in the ninth.
Sensing that he might be able to secure a memorable knockout, Chisora never stopped trying to put his opponent away. He sent Wallin to the canvas again in the final round, but Otto ultimately survived to see the closing bell.
Derek secured his 36th career win via scorecards of 117-109, 114-112 and 116-110, but Wallin more than played his part and earned Chisora’s eternal respect in the process.
“I’m disappointed, I tried,” admitted Wallin during a post-fight interview with iFL TV. “It wasn’t my night. Derek fought a great fight.” Otto also heralded the victor as one of the hardest punchers he’d been in the ring with.
“He has good power. He’s definitely one of the biggest punchers that I’ve been in with.” Given that Wallin has faced both Tyson Fury and Anthony Joshua, that is significant praise.