Former undisputed cruiserweight champion Oleksandr Usyk of Ukraine has been penciled to take on a longtime contender and former title challenger Dereck Chisora in a heavyweight encounter on May 23, 2020, at the O2 Arena in London. The bout was made official by Matchroom Boxing’s Eddie Hearn last March 11, 2020.

Usyk is taking a big risk in facing Chisora. The Ukrainian is in a mandatory position to challenge heavyweight ruler Anthony Joshua but with Joshua still having business against another mandatory challenger in Kubrat Pulev on June 23, 2020, Usyk isn’t waiting on the sidelines and is keeping himself busy against a dangerous opponent in Chisora.

Britain’s Chisora has faced the who’s who of the heavyweight division and he has been a contender for as long as I can remember. He challenged for the world title once but lost on points to Vitali Klitschko. He has been given up as washed up before but has kept on defying the odds. The thing with Chisora is that he’s lost all the big fights he’s been involved in. He has two losses to Tyson Fury and another pair against Dillian Whyte. He derailed David Price in his last bout and is looking to stop Usyk’s dream in London.

A win by Usyk here and a victory by AJ in June should set up an explosive world title fight possibly in the fall. But the Ukrainian can’t look too far ahead against a proven veteran like Chisora. Let’s take a look at who wins this all-important heavyweight matchup:

“Boxing" Undisputed Champion

Oleksandr Usyk is the first undisputed world boxing champion from Ukraine. He is the first cruiserweight to win the four major boxing belts ( WBC, IBF, WBA, and WBO ), the most recent boxer to win all four belts since Terence Crawford in 2017, and the fifth fighter in history to do so after Crawford, Jermain Taylor, Bernard Hopkins, and Cecilia Braekhus. The 33-year old Ukrainian boxer won gold medals at the 2011 World Championships and the 2012 Summer Olympics before turning professional in 2013. He is known for the speed of his accomplishments, winning a world title in only his 10th professional fight, and becoming the undisputed champion in his weight class in his 15th bout. He is ranked by The Ring as the 5th best pound for pound fighter on the planet.

The 2018 BWAA Boxer of the Year stands 6-3 tall with a reach of 78 inches while fighting out of the southpaw stance. Usyk unified the cruiserweight belts by winning the World Boxing Super Series cruiserweight tournament. He has an undefeated record of 17-0 with 13 knockouts and has beaten a total of five current or former world champions. After retaining his undisputed cruiserweight championship with an explosive 8th round KO of Tony Bellew, he vacated the belts and moved up to the heavyweight division.

What are the Moneyline Odds?

Oleksandr Usyk


Dereck Chisora


Odds from SportsBetting as of 03/18/20

“Boxing" War Chisora

Dereck Chisora is one of the more prominent fighters from the United Kingdom. The Zimbabwean-born fighter gained his fame by winning multiple heavyweight titles in the regional scene. Known as War Chisora, he held the British and Commonwealth heavyweight titles from 2010-2011 and the European title from 2013-2014. He once challenged for the WBC heavyweight title, losing by 12-round unanimous decision to Vitali Klitschko in 2012. Last October 2019, he won the WBO inter-continental heavyweight championship with a 4th round TKO of former Olympic bronze medalist David Price. He holds victories over notable heavyweight contenders Danny Williams, Kevin Johnson, Carlos Takam, and Artur Szpilka.

The 36-year old Londoner stands 6-1 tall with a reach of 74 inches while fighting out of the orthodox stance. He has a record of 32-9 with 23 wins by knockout. Chisora has a pair of losses to current WBC and lineal heavyweight champion Tyson Fury and he also lost to prominent fighters like David Haye, Robert Helenius, Kubrat Pulev, and most recently Dillian Whyte. Since his second loss to White, Chisora has picked up three consecutive victories, including back to back knockouts wins over Artur Szpilka and David Price.

“Boxing" Who Wins?

Chisora is at least two levels above Witherspoon whom Usyk forced to quit after seven rounds. Not only is Chisora a bigger puncher than Witherspoon, but he is also a fighter who applies excellent pressure on his opponents. Sure, he is undersized but he isn’t that small and he isn’t short in the heart.

The British fighter’s style could pose problems for the Ukrainian because he applies good pressure, attacks the body well, and has a very good overhand right. These will make it hard for Usyk to use all four corners of the ring and dominate the fight with his skill. Chisora is always on the front foot and this could cause take Usyk off his usual game plan. He’s also been the more active fighter in the last 18 months so that could be to his advantage as well.

That said, I think that Usyk is a class above Chisora when it comes to technical and fundamental boxing skills.

The Ukrainian is younger and has much less mileage than his opponent and he has beaten several fighters who are better than Chisora. Usyk also enjoys a two-inch height advantage pus a four-inch edge when it comes to reach. He will try to force Chisora to fight on his back foot but I don’t think the Brit will give him easy rounds here. Usyk will have to earn them hard.

The first half of this bout should be pretty interesting. I think Chisora will be relentless and he will also try to go for the kill early because he knows that Usyk is going to be tough to beat in a 12-round boxing match. I’m particularly interested in how Chisora’s body shots are going affect Usyk, if at all. I think we will have a competitive fight early but I think Chisora tires after round six. The Brit will move forward, take his chances, and miss a lot of punches. Usyk will fight back pedaling at first but his length and skill are going to allow him to win the rounds. When Chisora tires late, Usyk is going to chop him down like a tree. I’m picking Oleksandr Usyk to win by knockout after Round 8.

Prediction: Oleksandr Usyk

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