Predictions for Oleksandr Usyk vs Derek Chisora - who wins? why? betting odds preview

Predictions for Oleksandr Usyk vs Derek Chisora

Published On Thursday, March 12, 2020By British Boxing News

Oleksandr Usyk vs Derek Chisora - who wins?

Pound-for-pound star Oleksandr Usyk will face Briton Derek Chisora in a colossal Heavyweight clash at The O2 in London on Saturday May 23, live on Sky Sports Box Office in the UK and DAZN in the US.

33-year-old Usyk (17-0, 13KOs) is an Olympic gold medalist, a history-making undisputed cruiserweight world champion, and has successfully made his heavyweight debut against heavy-handed Chazz Witherspoon (38-4, 29KOs) last year.

Chisora (32-9, 23KOs) has enjoyed a late run of form in his career, which has seen him score nine knockouts in his past 10 victories. The 36-year-old Londoner comes into the contest having won all three of his contests last year.

With this information, BBN asked their panel of experts who wins this heavyweight headliner and why?


Kieran Gething
Welsh Area super-lightweight champion

"Usyk is another level, he may not have the stopping power some of the bigger guys have but I think he will give prolonged beatings to anyone in the heavyweight division!"


Ryan Walsh
British featherweight champion

"Usyk will win on points, his superior speed and footwork will be a major problem, plus the southpaw stance!

I’m a big Derek Chisora fan, so I hope he does the unbelievable and KO's Usyk. I just don’t see Oleksandr sticking around much for Del to land any bombs."


Mick Kane
Boxing Writer

"I fancy Usyk to win quite comfortably. He has the speed and the skill to dominate the fight but does he have the power at heavyweight to win by knockout. I can see a similar fight to Usyk v Bellew where Chosora could have some success in the early rounds before Usyk figures out how to control and dominate the fight. Usyk to win by referee stoppage around rounds 7-8."


Francy Luzoho
Super-lightweight prospect

"Great fight for both, but the winner in this fight is Usyk unless Derek lands a knockout punch from God, it’s going to be a long night or short.

Usyk is a student of the game, his jab and movement is going to play a big part of the fight, I don’t see the fight going six rounds with Derek's corner throwing in the towel."


Anish Parekh
British Boxing News Writer

"This is a significant fight for both men.

For Usyk, it's a chance to display his vast array of skills against a big, determined heavyweight, in a rich vein of form. Chisora, on the other hand, has a chance to cause a major upset but more importantly put himself in line for a shot against Anthony Joshua in what would be a huge career payday.

Chisora has flicked the switch in the past few years. He has become increasingly dedicated, looks in great shape and attempts to descend every contest into a war. This has culminated in some decent victories over gatekeeper and fringe contender-level fighters. He will pressure the decorated Ukrainian as soon as the bell rings and swarm him in an effort to disrupt his rhythm.

The problem for 'Del Boy', however, is that any time he has been confronted with a fleet-footed foe, he has struggled - Fury twice, Haye and Kabayel all flummoxed Chisora with their movement.

Usyk has the best footwork of any current day heavyweight. He has a great jab and puts together fluid combinations. The doubt looming over him is whether he can put a dent in a relentless Chisora, or whether he will be overwhelmed and ultimately overpowered by the naturally larger man.

In the heavyweight division anything can happen but I expect Usyk to get past Chisora. He will have to be cautious and make it cagey early on but once Chisora begins to tire, he will find his spots and let his hands go. The Brit will be brave and try to walk through punches to land his own but the accumulation of punishment will grind him down before his corner mercifully pull him out of the contest."


Ace Adam
Super-middleweight prospect

"I think this fight could go either way, either Usyk win via points or Derek via KO."


Matt Marsh
British super-bantamweight champion

"Usyk is going to do damage in the heavyweight division and he is starting off with a good win with Derek Chisora - a late stoppage for me."


Tony Tolj
Boxing Manager

"Usyk via UD, he will prove too skilled and crafty for Chisora.

Chisora has a puncher's chance but I can't see him winning on points.

Usyk could grind Chisora down and stop him late."


Paul Stevenson
Everton Red Triangle Head Coach

"Interesting fight. Chisora is established as a big dangerous heavyweight while Usyk despite his pedigree is untested against the big boys. Sometimes  the lighter man has the advantage and sometimes he doesn’t, it just depends on what each allows or makes the other do. Can’t see Usyk standing in front of big Del for long early on, he’ll try to box in circles around him. Can he hurt Chisora? I’d be surprised but anything’s possible. I see it going one of two ways, either Derek will be too big and busy for the smooth boxing Usyk or Usyk will be too skilful for the big dangerous Chisora. If Usyk is as good as people think he is he should win a decision but don’t write Chisora off."


Ben Day
Southern Area super-lightweight champion

"You surely have to pick Usyk, I think he’s really talented and a very good fighter; I like him. I think Derek Chisora is that gate keeper to the huge fights, if you beat him then you're in the big time. Chisora cracks me up though, he’s a mad man!"


Tim Rickson
Sports Agent

"Chisora has had a bit of a resurgence in the twilight of his his career, so kudos to him, I'm pleased that he's still competing at a high level 13 years on from his debut. However, three wins in 2019 against Senad Gashi (17-2), Artur Szpilka (22-3) and David Price (25-6) does not put him in the same category as someone like Oleksandr Usyk.

Since winning gold at the London 2012 Olympics, he hasn't put a foot wrong and he has fought the best fighters in the world at cruiserweight. I know it's only his second contest at heavyweight, but he has schooled bigger, heavier opponents like when he beat Joe Joyce in the World Boxing Series.

He hasn't done anything during his entire boxing career that would ever give you cause to bet against him. I haven't seen any faults or opportunities for opponents to exploit. He's a pound-for-pound superstar.

I think he does the same thing to Tony Bellew, where he patiently eases into the fight, gets into his rhythm, finds the chinks and openings, then ends the contest in the middle rounds between 6-8 - the corner may be forced to throw in the towel."


Matt Stanton
Boxing Trainer

"While Chisora retains the power to be dangerous, as we saw from the Takam fight, I think the bout with Gashi showed he is not going to be comfortable chasing down an opponent and I think Usyk will essentially dart in and out to score before moving out of range and making Chisora follow him around the ring.

No-one gets hurt, everyone gets paid. Usyk by wide decision."


Ryan Clark
Co-Founder of

"Ahhh Del boy, the perfect gate keeper to welcome Usyk into the heavyweight division. I think Chisora will do his best to teach Usyk what it’s like to get hit by a full scale heavyweight but, realistically, Usyk will be too clinical and box his way to an easy points win. I cant see him taking any risks to go for an impressive KO, I think he’ll get 12 rounds under his belt and keep things simple."


Aqib Tahlat
British Boxing News Writer

"I believe Dereck Chisora will be a threat to Usyk and it’s a very dangerous fight for him as he’s already the mandatory for Anthony Joshua’s belt. However this is probably the best fight to make for Usyk to see if he can be successful at the heavier division.

I believe Usyk will win this on points. I think he is technically one of the best and he will slowly and gradually break Chisora down mentally and physically.

It’s a great fight though and the fans are the real winners in this one."


Dee 'The Hat' Taggart
Boxing Trainer

"Usyk, for me, he’s a small heavyweight, but I can’t ever remember Derek winning a big fight to be honest. Who knows, maybe this will be the one."


Online Poll

Chisora points: 3%
Chisora KO: 14%
Usyk points: 31%
Usyk KO: 52%

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