Ten years, nine months and 15 days after his first tilt, British heavyweight veteran will have an improbable second shot at the WBC heavyweight title when he faces long-time rival Tyson Fury at Tottenham Hotspur Stadium on Saturday.
Chisora snapped a three-fight losing streak when he battled to a revenge victory over Kubrat Pulev in July, prevailing via split decision at the O2 Arena.
It was a popular outcome for a 38-year-old who has established himself as an unlikely folk hero of British boxing over recent years, but a fight for the title next up still felt improbable at that point.
However, as Fury became restless in his short-lived retirement after beating Dillian Whyte at Wembley in April, he called out old foe Chisora, who he beat in 2011 and then again in 2014.
What initially seemed like hot air intended to elicit social media amusement quickly escalated and, after a proposed bout between Fury and Anthony Joshua collapsed, Chisora was handed his outsider shot at glory.
Here, The Sporting News looks back over six of the most memorable fights of his career that have led to this unexpected crescendo.
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Vitali Klitschko vs. Derek Chisora — February 18, 2012
A quick glance at Boxrec shows the elder Klitschko successfully defended his WBC title against Chisora via a wide unanimous decision. The challenger was given two rounds by two judges and one on the third card. But this was the night when Chisora showed, contrary to many expectations, that he belonged at the elite level. In his typical style, he made Klitschko work incredibly hard for 36 minutes. The experienced champion earned a deserved victory, but certainly not a routine one.
This was just as well given Chisora’s antics before the fight, where he slapped Klitschko at the weigh-in and spat water in the face of his brother Wladimir in the ring, did little to ingratiate himself. Had he been dispatched and overmatched like the majority of Klitschko’s opponents since his bloody defeat to Lennox Lewis in 2003, he’d have likely been on the scrapheap as boxing’s latest failed ‘bad boy’. But Derek’s exploits during the bout — not to mention the post-fight press conference, where he infamously brawled with David Haye — meant everyone was keen to see what he did next.
Derek Chisora vs. Malik Scott — July 20, 2013
Chisora and Haye both had their licenses revoked by the British Boxing Board of Control (BBBofC) after their scrap in Munich, meaning the bizarre situation of their Upton Park stadium fight in 2012 taking place under the auspices of the Luxembourg Boxing Federation. To continue a theme that would be repeated numerous times later on in his career, Chisora acquitted himself very well as the underdog, discomforting Haye over the opening four rounds. However, he was stopped for the first time in his career in the fifth, decked twice by the former cruiserweight and heavyweight king.
Coming on the back of the Klitschko loss, a disputed split-decision reverse against Robert Helenius for the European title and a lacklustre defeat in his first bout with Fury — where Chisora was under-motivated and overweight — his record now read four defeats in his past five bouts. A rebuilding phase followed, with five victories in the space of 10 months for the newly lean Del Boy.
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The most impressive of these came against the previously undefeated American Malik Scott. A rangy, slick operator lacking significant heavyweight power, Scott had plenty of success against Chisora, whose rough housing and excellent work to the body started to have an impact. The sixth was Chisora’s best of the contest and he dropped Scott with a chopping right hand before controversy struck again. Scott took a knee for the eight count, was up at nine but the bout was waved off by referee Phil Edwards. As unsatisfactory as the ending was, Chisora was again on his way back to fights with the big names in the division.
Dillian Whyte vs. Derek Chisora — December 10, 2016
A rematch with Fury ended the winning run, with the Gypsy King giving the first full indications of his true potential throughout a masterful display. Chisora was pulled out at the end of the 10th round and a couple of years on undercards and in boxing backwaters followed, with the exception of his loss to Pulev for the European title in May 2016.
He won five times either side of that bout against unheralded opposition before being selected to fight Dillian Whyte on the undercard of Joshua’s blowout title defence against John Molina. The pair feuded on social media in the months leading up to the fight and the BBBofC withdrew its sanction for the bout after Chisora infamously threw a table at Whyte during the final press conference.
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What followed far surpassed that unsavoury pantomime as Whyte and Chisora produced one of the finest heavyweight fights of the decade. Chisora rocked his foe with left hooks in round five and had him in trouble on the ropes. The eighth brought thrilling toe-to-toe trading and Whyte needed the bell after soaking up a thudding left uppercut. Chisora looked like he had him going again early in the 10th and during a sensational final round before dropping a razor-thin split decision.
Derek Chisora vs. Carlos Takam — July 28, 2018
The Whyte rematch did not immediately materialise and Chisora needlessly lost momentum with a listless loss to Agit Kabayel, continuing a cursed relationship with the European title. He was swinging in the last chance saloon against former world title challenger Carlos Takam on the undercard of Whyte’s clash with Joseph Parker.
Takam was a swarm of activity throughout and hurt Chisora in round six before his fellow veteran came firing back off the ropes before the bell, despite being on unsteady legs. The O2 Arena roared, demonstrating how a once-divisive figure had graduated to the status of cult hero. In round eight, Chisora gave them exactly what they wanted. After a relentless, back-and-forth seventh, a huge overhand right sent Takam to the canvas. He rose groggily but Chisora immediately administered a repeat dose for a stunning KO victory.
Derek Chisora vs. Artur Szpilka — July 20, 2019
Victory over Takam finally earned Chisora the Whyte return and, despite again pushing his rival to the brink, he was flattened by a chilling round-11 left hook. A forgettable points win over a gun-shy Senad Gashi followed before a return to one of Whyte’s undercards against former Deontay Wilder foe Artur Szpilka.
What it took knockout specialist Wilder nine rounds to accomplish, Chisora did in two. A big right hook had Szpilka out on his feet near the ropes before he was battered limply to the floor. It was a showreel triumph for Chisora and another win in quick time against David Price followed.
Derek Chisora vs. Kubrat Pulev — July 9, 2022
The victories over Szpilka and Price set up a shot at Oleksandr Usyk. Chisora went the distance with the masterful Ukrainian to lose on points, as he did twice against Parker — the first time more contentiously than the second. As creditable as each of those defeats were, boxing’s most unlikely box office attraction needed a W to remain at the top table.
With it all on the line, he delivered in a knife-edge encounter with Pulev. In a back-and-forth contest, where the Bulgarian’s cleaner boxing at range was offset by Chisora bulldozing work rate, it again went to the cards. Unlike in those first bouts with Parker and Whyte, a split decision went in his favour. Despite some expressing wishes for that to be his swansong, Chisora now faces his biggest against-the-odds assignment yet against Fury.
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