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Derek Chisora Names Toughest Opponent He’s Faced

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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

Derek Chisora waves to the crowd

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.

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Mateus Fernandes Wants to Join Tottenham After Bigger Offer Than Man Utd

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Tottenham Hotspur are trying to beat Manchester United to the signing of West Ham United midfielder Mateus Fernandes, and they have received a huge boost in their pursuit, according to the Independent.

Tottenham fans would have been excited when Fabrizio Romano dropped the bombshell earlier this month that they were working on a deal to sign Newcastle United midfielder Sandro Tonali, and that feeling would have only increased further after David Ornstein confirmed that Roberto De Zerbi also wants to sign Fernandes in a separate deal to the Italy international.

Man United have been viewed as the frontrunners to sign the 21-year-old for weeks now, having entered talks with the player and his agent over personal terms.

One report has claimed that the player has agreed to join after being happy with the financial offer, with the player said to be keen to link up with compatriot and idol Bruno Fernandes at Old Trafford as he looks to avoid playing Championship football next term.

However, Spurs are serious about landing the Portugal international, and they are willing to go to big lengths as club chiefs look to deliver a fourth signing of the summer for their Italian boss.

Tottenham Make Bigger Offer Than United for Fernandes

West Ham United midfielder Mateus Fernandes celebrates scoring Premier League goal against Sunderland via Reuters

According to the Independent, Tottenham have now made headway in the battle with United to sign Fernandes.

Spurs are said to have held positive talks with West Ham over a potential deal, with De Zerbi being backed with a significant summer transfer budget.

The Hammers are demanding £85m for their ‘superstar’ player, and they want a significant portion of that fee paid upfront, with Tottenham already offering a higher overall package than the Red Devils.

De Zerbi is a huge fan of Fernandes and Spurs have also launched a salary offer higher than United’s as they look to come out on top in this transfer battle.

Crucially, the report adds that the Portugal international is ‘very keen’ on a switch to the Tottenham Hotspur Stadium, which would also allow him to carry on living in London.

United don’t want to get involved in a bidding war and could walk away from a deal and look at alternative targets.

England World Cup Quiz

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out of 20

Romano: Tottenham Want to Sign Impressive World Cup Star

Cody Gakpo Annegret Hilse via Reuters

As well as transforming their central midfield options, Tottenham are also looking to make changes all across the frontline too.

Spurs remain in talks to sign Manchester City left-winger Savinho, but they are clearly looking at alternative targets to the Brazilian with progress slow on agreeing a deal with the Premier League runners-up.

One of those is Liverpool star Cody Gakpo, with Romano confirming that De Zerbi and Tottenham do have an interest in the Netherlands international.

The Dutchman had already been linked with a summer move away from Anfield even before they signed Victor Munoz, with the Spain international usually operating from the left flank.

It remains to be seen if that addition could spell the end for Gakpo at Anfield, but his performances for his country at the World Cup are only showcasing his ability, with two goals and an assist in the latest 5-1 win against Sweden.

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Mateus Fernandes Wants to Join Tottenham After Bigger Offer Than Man Utd

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Tottenham Hotspur are trying to beat Manchester United to the signing of West Ham United midfielder Mateus Fernandes, and they have received a huge boost in their pursuit, according to the Independent.

Tottenham fans would have been excited when Fabrizio Romano dropped the bombshell earlier this month that they were working on a deal to sign Newcastle United midfielder Sandro Tonali, and that feeling would have only increased further after David Ornstein confirmed that Roberto De Zerbi also wants to sign Fernandes in a separate deal to the Italy international.

Man United have been viewed as the frontrunners to sign the 21-year-old for weeks now, having entered talks with the player and his agent over personal terms.

One report has claimed that the player has agreed to join after being happy with the financial offer, with the player said to be keen to link up with compatriot and idol Bruno Fernandes at Old Trafford as he looks to avoid playing Championship football next term.

However, Spurs are serious about landing the Portugal international, and they are willing to go to big lengths as club chiefs look to deliver a fourth signing of the summer for their Italian boss.

Tottenham Make Bigger Offer Than United for Fernandes

West Ham United midfielder Mateus Fernandes celebrates scoring Premier League goal against Sunderland via Reuters

According to the Independent, Tottenham have now made headway in the battle with United to sign Fernandes.

Spurs are said to have held positive talks with West Ham over a potential deal, with De Zerbi being backed with a significant summer transfer budget.

The Hammers are demanding £85m for their ‘superstar’ player, and they want a significant portion of that fee paid upfront, with Tottenham already offering a higher overall package than the Red Devils.

De Zerbi is a huge fan of Fernandes and Spurs have also launched a salary offer higher than United’s as they look to come out on top in this transfer battle.

Crucially, the report adds that the Portugal international is ‘very keen’ on a switch to the Tottenham Hotspur Stadium, which would also allow him to carry on living in London.

United don’t want to get involved in a bidding war and could walk away from a deal and look at alternative targets.

England World Cup Quiz

You scored

out of 20

Romano: Tottenham Want to Sign Impressive World Cup Star

Cody Gakpo Annegret Hilse via Reuters

As well as transforming their central midfield options, Tottenham are also looking to make changes all across the frontline too.

Spurs remain in talks to sign Manchester City left-winger Savinho, but they are clearly looking at alternative targets to the Brazilian with progress slow on agreeing a deal with the Premier League runners-up.

One of those is Liverpool star Cody Gakpo, with Romano confirming that De Zerbi and Tottenham do have an interest in the Netherlands international.

The Dutchman had already been linked with a summer move away from Anfield even before they signed Victor Munoz, with the Spain international usually operating from the left flank.

It remains to be seen if that addition could spell the end for Gakpo at Anfield, but his performances for his country at the World Cup are only showcasing his ability, with two goals and an assist in the latest 5-1 win against Sweden.

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Spurs Have Already Sealed £8.5m Transfer Better Than Fernandes

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Tottenham Hotspur’s owners are putting their money where their mouths are and backing new head coach Roberto De Zerbi in the summer transfer market.

Spurs have finished 17th in the Premier League in back-to-back seasons, failing to live up to the ‘big six’ billing. They only survived in the top flight on the final day of last season, beating Everton 1-0 to stave off relegation to the Championship and condemn fierce rivals West Ham United to the second tier instead.

De Zerbi rescued the club in the final two months of the campaign, saving them from what looked like a perilous position.

Now the plan is clear – for a season like that to never happen again.

Spurs owners are following through with their vow to invest in the squad

Roebrto De Zerbi celebrates Spurs' win over Everton via Reuters

The Lewis Family, who own the club, made a statement to the fans after the final game of the season, saying: “We take responsibility for rebuilding Spurs. Our ambition is to recapture the spirit of the club and bring back the excitement, the fearlessness and the bold football we have always felt defined us. That means football comes first. The board and executive team have laid out their plans to meet this ambition.

“This will require investment – in our teams, the academy, our backroom functions and more – and we are fully committed to this. We are not selling the club. We are all in. We are investing in it. You will see more of this in the coming months.”

That vow has already bore fruit with three defensive signings arriving at the club early in the transfer window. Andy Robertson, Marcos Senesi and Jan Paul van Hecke have already joined the De Zerbi revolution in N17 and more signings are set to follow.

After addressing the defence – Spurs have conceded 246 goals in the last four Premier League seasons combined – the Italian has turned his attention to the midfield department.

They have seen one bid of around £75million rejected by Newcastle for Sandro Tonali, while there are talks over bringing Mateus Fernandes to the club from West Ham. Spurs face a battle with Manchester City for Tonali and Manchester United for Fernandes, with reports suggesting it is not one or the other, but that the Lilywhites would be keen to add both to their ranks.

But with a new plan to bring in big-money signings and change to a more ‘win now’ approach, there are sure to be some painful decisions to be made with current members of the squad.

Two young players are ready to leave Tottenham

Luka Vuskovic via Reuters

And that is already being seen, with talk of two talented youngsters wanting to leave the Tottenham Hotspur Stadium in search of more game-time elsewhere. Nineteen-year-old defender Luka Vuskovic has been the subject of two bids from Brighton & Hove Albion, having impressed on loan with Hamburg in the Bundesliga last season. He is a highly-rated centre-back reportedly keen to leave having never made an appearance for the Lilywhites.

There is a feeling that Vuskovic, who started Croatia’s World Cup opener against England, could go on to become a £100million player if nurtured the right way.

And then there’s Lucas Bergvall, the 20-year-old Swede whom Spurs beat off competition from Barcelona to sign in 2024 for just £8.5million.

You scored

out of 20

Bergvall got perhaps more game time than he would have expected in the 2024/25 season due to a wealth of injuries to first-team stars, but did not look out of place at all, becoming a firm fans’ favourite in Ange Postecoglou’s second season and winning all three of the club’s end of season awards.

Three different managers and Spurs battling relegation stunted his opportunities in 2025/26 and with big-money signings being touted and having only played 113 minutes under De Zerbi in the final seven games of the season have led to the 20-year-old seeking pastures new too.

As Mauricio Pochettino alluded to in 2019, before he was sacked, a painful rebuild was required and seven years later it looks like that is finally happening and supporters may have to come to terms with some decisions that, on the face of it, look very strange and disappointing.

Bergvall would be a painful loss at Spurs

Lucas Bergvall in action for Tottenham against Newcastle in the Premier League

Bergvall falls into that category. Signing Tonali, a ready-made, 26-year-old midfielder makes a lot of sense. Signing Fernandes, while letting Bergvall go, however, does not.

The Hammers star has two years’ experience in the Premier League – like Bergvall – and is aged just 21, a year older than the Swede.

Fernandes also has two relegations to his name, having gone down with Southampton before making the move to the London Stadium last summer and then suffering the same fate.

Now that is not all his fault, of course, but does Fernandes, offer anything better than Bergvall, given they both play in the same position and both prefer to be an 8 rather than a 6?

True, we’ve probably seen more of what Fernandes is capable of, but Bergvall being buffeted around the pitch, playing as a 6 a 10 and even wide does him a disservice. We really need to see what he can do in his favoured position on a regular basis before just discarding him.

And then there’s the price tag. West Ham want around £80million to sanction a deal for Fernandes. Spending that kind of money on Tonali again makes complete sense, but doing it twice, for a player who may or may not be better than what you already have, who cost just £8.5million is confusing.

Ask any Spurs fan and they will tell you they have been waiting a long time for the club to truly invest and embrace a win now approach rather than being in transition and ‘building for the future’. Bergvall may well be for the future, but he has already shown he is for the here and now too and is probably just as good, if not better, than an £80million Fernandes and that is why his exit will really hurt.


Lucas Bergvall in action for Tottenham Hotspur


Fabrizio Romano Reveals How Much Tottenham Will Sell Lucas Bergvall For

Spurs signing Tonali could come at a greater cost than a giant fee alone

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