Biggest deadline day transfers ever from Ozil to Arsenal and Rooney and Ronaldo to Man Utd – but were they a success?

IT’S that time of year when the Premier League’s biggest clubs make astonishing moves in the transfer market.

Deadline day sees our elite sides splashing the cash on the biggest names in football.

Mesut Ozil was a surprise signing by Arsenal on transfer deadline day

Despite flashes of his talent, Ozil underachieved at the Gunners

But, just because they pay outrageous fees and salaries, it doesn’t always represent value for money.

SunSport looks at 10 huge signings that have caught the eye over the years.

We also lift the lid on how they fared following their blockbuster moves. Check out our verdicts below…

Mesut Ozil – Real Madrid to Arsenal

In 2013, at the eleventh hour, Arsene Wenger pulled off the unthinkable when he brought the best playmaker in Europe from Real Madrid.

It was a huge statement signing by the Gunners, who splashed a whopping £42million on the German.

He was named Arsenal’s player of the season in 2015-2016, and made 184 Premier League appearances, scoring 33 goals and producing 54 assists.

However, he was bombed out of the Emirates when Mikel Arteta arrived at the club – partly because of his huge £350,000-per-week salary in 2021.

Arteta said: “Mesut’s achievements at Arsenal are undisputed”.

SunSport’s view: Underachieved at the Emirates.

Cole Palmer – Man City to Chelsea

Another transfer that came out of the blue, Palmer swapped Manchester for London in a £42.5m deal last summer.

He needed to leave Man City for game time, while Chelsea wanted a talisman.

They found it in Palmer, who went on to be one of the players of the season last campaign.

He scored 25 goals in all competitions, and scooped the Hublot Young Player of the Season awards, as well as the PFA Young Player of the Year.

SunSport’s view: Hit – he is already on his way to legend status at Stamford Bridge.

Cole Palmer has become one of the Premier League’s players since signing for Chelsea

Cristiano Ronaldo – Juventus to Man Utd

There is an argument to be had that you should never return to a club you were once a hero.

Ronaldo originally left United for Real Madrid in 2009, won everything, then moved to Juventus.

Unbelievably, the Red Devils snatched him from the Italian giants for £13m, believing at 36 he still had loads to offer.

He scored 24 goals in 38 games in his first season, but found himself frozen out when Erik Ten Hag was appointed as United boss.

An interview with Piers Morgan further made his position untenable and he moved to Saudi Arabia.

SunSport’s view: 24 goals in all competitions is enough to tell you he did his job well.

Cristiano Ronaldo’s return to Old Trafford was heralded a masterstroke

An interview with Piers Morgan was the final nail in the coffin for Ronaldo’s Utd career

Wayne Rooney – Everton to Man Utd

Rooney, at 18, was the most in-demand teenager in Europe.

That’s why Man Utd splashed £30m on him in 2004. Incredibly, he scored a hat-trick on his debut in the Champions League.

He would go on to win 13 major trophies, including five Premier League titles, four League Cups and the Champions League, the FA Cup, Europa League and FIFA Club World Cup once.

Better still, he would break Bobby Charlton’s long all-time goalscoring record – scoring 253 goals for the club.

SunSport’s view: Probably the best deadline day signing ever.

Wayne Rooney cost £30million in 2004 when he signed from Everton

Rooney would go on to break Man Utd’s goalscoring record set by Bobby Charlton

Dimitar Berbatov – Spurs to Man Utd

In 2008, Tottenham’s languid Bulgarian striker – a crowd favourite – was snapped up by Sir Alex Ferguson in a £30m deal.

There were doubts whether he could fit into Utd’s style of play, but he soon put those fears to bed.

In his four seasons, he won two Premier League titles, the League Cup and the Club World Cup.

He also shared the Golden Boot in 2010 with Carlos Tevez after scoring 20 times that season.

SunSport’s view: An astute signing and class act.

Dimitar Berbatov proved to be an inspired signing from Spurs

Ashley Cole – Chelsea to Arsenal

After refusing a contract with the Gunners, Cole was swapped for William Gallas plus £5m in a deal that took him to Chelsea.

It was an outrageous swoop that caused a stink in North London, with Arsenal fans unfairly dubbing him ‘Cashley’ Cole.

Cole would lift the Premier League with Chelsea in 2010, as well as four FA Cups, the Champions League and Europa League.

He also improved as a defender under Mourinho’s stewardship.

SunSport’s view: Great at Arsenal, but even better at Chelsea. Big hit.

Ashley Cole controversially moved to Chelsea, much to Arsenal fans’ annoyance

Cole would end up becoming a Chelsea legend and win the Champions League

Manuel Akanji – Dortmund to Man City

Akanji was snapped up by Guardiola for a bargain £15m in 2022.

And as first seasons go, winning the treble in his debut campaign was the perfect introduction.

The Swiss defender has seemingly fitted into City’s style and is one of the first names on the teamsheet.

At 29, he’s coming into his prime.

SunSport view: A masterstroke signing for the price and quality of the player.

Manuel Akanji’s £15million signing was a bargain and masterstroke

Claude Makelele – Real Madrid to Chelsea

The Frenchman, bizarrely, found himself surplus to requirements at Real Madrid.

Chelsea stepped in in the summer of 2003 – paying a then whopping £16m to bring the midfielder to the club.

Then manager Claudio Ranieri declared he would be the “battery” of the team, and he wasn’t wrong.

He would win consecutive league titles with the Blues, before ending his career at PSG.

SunSport’s view: Unspectacular, but incredibly effective. Another success story.

Claude Makelele proved to be a very effective buy for Chelsea

Enzo Fernandez – Benfica to Chelsea

The Argentina World Cup winner’s astounding £107m move last January completed a £323m transfer splurge by Todd Boehly in his first season as Chelsea co-owner.

But, in truth, Enzo’s move from Portuguese giants Benfica has been a disappointment.

So far, he has failed to justify his price tag, although his transfer fee wasn’t his own doing.

However, he has still found it difficult coping with the demands of English football.

SunSport view: Jury’s still out, and at 23 he has time to prove himself.

Jury is still out on Enzo Fernandez’s £107million move to Chelsea

Antony – Ajax to Man Utd

In 2022, a mammoth £80m was handed over to Ajax for Brazilian winger Antony by United.

He was championed by manager Erik Ten Hag, who got the best out of him in the Netherlands.

However, he has struggled for form at Old Trafford and has now found himself frozen out of the team.

Incredibly, it has been suggested he might get sold for a pittance of the fee paid. But who would take him now?

SunSport’s view: Biggest flop on transfer deadline day? Only Enzo can beat him to that.

Antony has been a huge flop at Man Utd after £80m was spent on the Brazilian