Arsenal and Manchester United dominate the most expensive summer transfer deadline day deals ever

Matt Stead
Arsenal player Mesut Ozil and Arsene Wenger
Arsenal signing Mesut Ozil was just the best fun, wasn't it?

It will take some doing to top the fees on this list because Arsenal and Manchester United have left it late to complete some huge transfers in the past.


8) David Luiz – £34m (PSG to Chelsea, 2016)
Antonio Conte needed a centre-half with ball-playing capabilities; Chelsea knew the perfect candidate for the role. Few expected David Luiz to return to the Premier League when a Playstation-adjacent 10-year-old controlled him all the way to Paris Saint-Germain in 2014, his reputation as an error-prone, untrustworthy defender assured. He was back two years later to decry the doubters.

It was always an unfair millstone hanging around the Brazilian’s neck. He was impulsive but intelligent, more risk perverse than averse, yet still a supremely gifted player. And Luiz proved as such by playing an integral role in Chelsea’s first title win since 2010 on his return, earning himself a place in the PFA Team of the Year as a result. Adding an FA Cup and Europa League to his trophy cabinet before leaving to be a bit rubbish for Arsenal only strengthened his legacy.


7) Danny Drinkwater – £35m (Leicester to Chelsea, 2017)
Twelve months later, Chelsea were signing another influential title winner late in the window to play a central role in the upcoming campaign. That it ended in an actual apology half a decade later says an awful lot.

The midfielder started 12 games in five years at Stamford Bridge, last featuring for them in the Premier League in March 2018 before being sent on four different loans, including two underwhelming top-flight spells with Aston Villa and Burnley. Drinkwater remains unattached but unretired since his 2022 release.

Danny Drinkwater during a match

Danny Drinkwater struggled at Chelsea


6) Alex Oxlade-Chamberlain – £35m (Arsenal to Liverpool, 2017)
“It would be not fair to put the defeat at Liverpool, where the whole team had a bad performance, on one player,” said Arsene Wenger in December 2017, the wounds from a 4-0 shellacking at Anfield four months prior having barely healed. Alex Oxlade-Chamberlain was as hopeless as his teammates in that defeat, so much so that he decided to swap shirts permanently four days later.

His Liverpool career picked up where his Arsenal one left off, the midfielder debuting for the Reds in a 5-0 loss to Manchester City. Oxlade-Chamberlain did not start in a Premier League win under Klopp until November, struggling to establish himself in the side. But just as a stumble started to turn into a sprint, the England international was stopped in his tracks by a serious knee injury in a Champions League semi-final.

Oxlade-Chamberlain flitted in and out of the first team for the following five seasons before his exit, with 146 games and five trophies in his back pocket.


5) Alex Iwobi – £35m (Arsenal to Everton, 2019)
There might be another deadline day move in the offing for Iwobi, at least if Fulham get their own way. But at least the general public has been warned this time; Everton’s interest in August 2019 only really became known when the fabled deal sheet was submitted hours before the window shut.

The Toffees had finally abandoned a move for Wilfried Zaha and eventually sought to move on to someone Marco Silva laughably described as “one of our main targets for this window”. Arsenal understandably snapped their hands off.


4) Mesut Ozil – £42.4m (Real Madrid to Arsenal, 2013)
The Gunners were similarly eager to complete what was a truly extraordinary club-record signing at the time. It really was quite a remarkable coup. Perhaps our most enduring memory of Ozil until those fans flocked to the Sky Sports cameras in the late hours of September 2 and early yawns of September 3 were of the German running rings around Gareth Barry at the 2010 World Cup. That was enough to whet the appetite of a Premier League desperate to replace the star power of the departing Gareth Bale.

As it happened, that was the move that precipitated Ozil’s arrival. Arsene Wenger described it as a “domino effect” that allowed Arsenal – who had previously signed just Yaya Sanogo and Mathieu Flamini all summer – to sneak in at the final hour. For a long old while it was beautiful and often difficult to comprehend, but the stardust had slowly dissipated by the time Arsenal cancelled his lucrative contract prematurely in 2021.


3) Anthony Martial – £44.7m (Monaco to Manchester United, 2015)
‘WHAT A WASTE OF MONEY’ indeed. That Daily Mirror back page is dredged up whenever Anthony Martial hits a run of form – it used to happen, promise – but it really was a stunning investment in a completely unproven product at the time. Manchester United parted with an initial £36.7m for a player whose entire career comprised of 41 first-team starts.

It was almost worth it for that debut alone. The sudden burst of pace, the footwork, the public assassination of Martin Skrtel, the opening up of the body, the curl into the corner, the Martin Tylergasm – the grand arrival.

That remains the zenith of his Old Trafford rollercoaster, which has unfortunately included more nadirs than expected. The clauses in Martial’s deal to take the figure up to £56.7m were described as “very realistic” by Monaco, despite one of them being that he would win the Ballon d’Or by June 2019. Up until this summer he was the Premier League’s most expensive teenager ever.


2) Thomas Partey – £45m (Atletico Madrid to Arsenal, 2020)
The first summer of Mikel Arteta and Edu at Arsenal was quite the ride. The first three signings were Pablo Mari, Cedric Soares and Willian. The two most expensive were Gabriel and Partey. Absolutely wild.

Partey was the fourth-most expensive signing in Arsenal history at the time, rather lazily described by some as Patrick Vieira’s long-awaited successor at first. Time has informed us otherwise: as good as Partey can be, he is neither a) elite, nor b) a right-back.


1) Antony – £82m (Ajax to Manchester United, 2022)
One of the great overpays of all time
. Ajax had already sold Ryan Gravenberch, Sebastien Haller, Lisandro Martínez, Nicolas Tagliafico and Perr Schuurs to the tune of about £100m so had no financial desire to cash in on Erik ten Hag’s primary target. But Manchester United just kept pushing.

As Edwin van der Sar, Ajax chief executive at the time, put it: “We would have liked to keep him here one year longer – there was not a dire need to sell him, we had money in the bank – but the fee got so high. We challenged United to go as far as possible.” And the daft sods obliged.