Derek Chisora faces Deontay Wilder on Saturday night and our boxing expert Chris Oliver previews the action.
Boxing betting tips: Saturday action
2pts Derek Chisora to win by decision 10/3 (bet365)
1pt Mateusz Masternak to win 10/3 (bet365)
Derek Chisora and Deontay Wilder attempt to roll back the years as the pair of veterans headline at big show at London’s O2 Arena on Saturday night, live on DAZN PPV.
Both men are past their best and each will be having their 50th fight as a professional this weekend, but there is still plenty of interest in this one.
These two huge characters have provided so much entertainment in and out of the ring over the years and they will surely bring whatever they have left in an attempt to deliver one last exciting contest.
It may not be a bout of the highest standard, with retirement beckoning for the loser, but neither of them will want to go out on a defeat and they will be desperate to ensure they don’t add another notch to their loss column.
When the fight was first mooted a few years ago, it was considered a very dangerous one for Chisora and it was thought he would be on the wrong end of a highlight reel knockout. However, their vastly differing fortunes in more recent times mean it is Chisora who enters as 8/13 favourite now and Wilder can be backed at 17/10.
Chisora brings a record of 36-13 (23 KOs) to the table after an up-and-down career which has seen him take on some of the biggest names of the last 20 years and, win or lose, he has always given it his all.
His journey looked to be at an end when he was put out of his misery in the 10th round of his trilogy fight with Tyson Fury in December 2022, but he has won all three outings since and has found some momentum in his Indian summer with those trio of points victories. The 42-year-old outlasted Gerald Washington in 2023, before dropping and outworking Joe Joyce the following year and then he produced arguably the best win of his career against Otto Wallin 14 months ago.
Chisora showed his typical guts and determination to battle through a cut eye for a unanimous decision verdict and even dropped the Swede twice in the final third of the fight. In what he promises will be his last outing (will he really call it a day if he wins?), we know what we’re going to get from ‘War’, who brings constant pressure and will look to get on the chest of his taller opponent.
Wilder (44-4-1) was once the most feared man in boxing, boasting a sledge hammer of a right hand that has seen him emerge with a knockout in all but one of his victories. That is a remarkable stoppage ratio and he got back to winning ways when halting Tyrrell Anthony Herndon (24-5) in the seventh round when last seen in June 2025.
However, he didn’t look great in that outing against lacklustre opposition and it was a far cry from ‘The Bronze Bomber’ who terrorised the heavyweight division in the previous decade. The man from Tuscaloosa, Alabama defended the WBC title 10 times before losing it to Tyson Fury in 2020 and he has been on a steady decline since.
That began a run of four losses in five fights, with Fury stopping him in their third battle before Joseph Parker outboxed him for a decision and Zhilei Zhang flattened him in five rounds. In those latter two defeats, Wilder looked gun-shy and his once-famous firepower seemed a thing of the past.
They were both trickier opponents than Chisora, though, and one thing is for certain – Wilder won’t have to go looking for the Finchley man, who will be right in front of the American and the last thing a fighter loses is his punch.
If Wilder still has some of that power left, then he could easily walk Chisora onto a big right hand and end this one for stoppage number 44. His best chance of doing so looks to be early doors and it is 5/2 about Wilder getting the job done inside the distance.
That said, detonating his bombs has become increasingly tricky for Wilder of late and even when he has found the target with his power shots, they haven’t had quite the same effect.
Wilder was always technically very limited and his power got him out of jail on several occasions, so if you take that right hand away then you’re left with a 6’6” fighter with not too much skill.
The shorter Chisora is capable of rolling under shots very well, especially against longer opponents like Wilder, and he is much more effective on the inside if he can get past the longer levers of the underdog. Chisora can score points when up close with his short hooks and bullying tactics, while his big overhand right has brought him a lot of success in recent years.
The Briton is durable, too, and his never-say-die attitude could be the deciding factor here. If Wilder isn’t able to deter the favourite’s advances, then he could be in for a very long night and, while it may not be pretty, I expect Chisora to fair best if this turns into a dog fight.
With both men in their forties and having seen much better days, I wouldn’t be surprised to see a slow pace and plenty of holding, with not as much action as we are being promised. As work-rates slow and this becomes a gruelling affair, that is where Chisora can gain the upper hand and possibly claim the biggest scalp of his career.
It is only 7/5 that he does so by stoppage and given that three of Wilder’s four defeats have come via this method, then it’s no surprise to see that priced up so short. However, Chisora hasn’t stopped anyone since he beat David Price in October 2019 and I wouldn’t be rushing to back him to change that here.
There is every chance this could turn into an ugly, drawn-out affair with little quality and lots of heart. Therefore, I am tempted in by the 10/3 about Chisora claiming a decision after 12 rounds of far-from-vintage fare, with his momentum earning him the nod from me.
The cult status of the two men, especially Chisora, will mean there will be plenty of eyeballs on this nostalgic dust-up but, a bit like a car crash, many may have wished they had turned away by the end of it.
Masternak to roll back the years
The most intriguing bout of the undercard is the cruiserweight clash between the unbeaten Viddal Riley and veteran Mateusz Masternak.
Riley took his record to 13-0 (7 KOs) with a fine display of boxing when outpointing Cheavon Clarke at Tottenham Hotspur Stadium just under a year ago and he’s a hot 3/10 favourite to record another victory here.
However, this is by far his toughest test to date and I don’t want to take those prohibitive odds as he faces a man who has mixed with some of the best at 200lbs in recent years.
Masternak (50-6, 33 KOs) may be 38 but he has only lost to world champions (future or past) in his last 18 bouts over a 10-year period, with a pair of points defeats to Tony Bellew and Yuniel Dorticos before he retired with a rib injury against Chris Billam-Smith in late 2023.
Let’s not forget he was ahead on the cards and giving Billam-Smith all sorts of problems up until the injury and he has won all three outings since.
The youth and skills of Riley could be too much for the older man, but Masternak’s experience at the very highest level can count for a lot and he looks a big price at 10/3 based on the Billam-Smith fight.
I am willing to take a chance at those odds in a fight I see as being much more evenly matched than the betting suggests and where the inexperience of Riley could land him in deep waters.
Posted at 11:40 BST on 03/04/26
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