Premier League biggest transfers: Where does Enzo Fernandez rank in list of most expensive fees and major flops?

Dom Farrell

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Premier League biggest transfers: Where does Enzo Fernandez rank in list of most expensive fees and major flops? image

Chelsea fans celebrated the biggest deal of the Todd Boehly era on January transfer deadline day as Argentina World Cup star Enzo Fernandez joined from Benfica.

The move is biggest fee paid out in British football history, with no player having ever commanded a greater fee than the £106.8m it took to secure Fernandez.

The 22-year-old midfielder was Chelsea's eighth signing of the mid-season window, with Ukraine winger Mykhailo Mudryk joining him on the list of most expensive Premier League transfers.

However, in recent years, the biggest transfer outlays in the richest league have rarely worked out exactly how all parties hoped, as the list below shows.

MORE: Declan Rice transfer news updates, reports and rumours with Arsenal, Man City chasing West Ham captain

1. Enzo Fernandez (Benfica to Chelsea, 2023): £106.8m

Benfica were bruised by a month-long saga that, until the final days of trading, looked set to conclude with Fernandez staying in Lisbon. They can console themselves with the gargantuan fee received for a player who cost them a mere £10m from River Plate last June.

Fernandez was already on the radar of major clubs across Europe, before a key role in Argentina's World Cup triumph sent him into the stratosphere. As he did in the opening defeat to Saudi Arabia, Fernandez came off the bench to score a game-sealing goal in the nervy 2-0 win over Mexico and was then a mainstay on the road to glory.

Chelsea hoped he would have a similarly transformative effect upon a Blues side needing a midfield refit, although the fact the World Cup final win over France was only his 10th senior cap underlines how much this outlay on an obviously gifted player is a bit of a punt.

2. Jack Grealish (Aston Villa to Man City, 2021): £100m

Grealish enjoyed a central role in Man City's 2022/23 treble win, with the England international turning a corner, after a tricky spell for Pep Guardiola's side in 2021/22, with just five top-flight goals in 18 months at the reigning champions.

His price tag weighed heavy last season with the former Aston Villa captain struggling to recapture the form which persuaded Guardiola to make his move.

However, after ending the domestic season with five goals and seven Premier League assists, he started City's Champions League final win over Inter Milan, with his antics in the week after elevating him to global fame, as his fee becomes less of a talking point.

3. Romelu Lukaku (Inter Milan to Chelsea, 2021): £97.5m

Fresh from their surprise run to Champions League glory under Thomas Tuchel, Lukaku was supposed to be the final piece in the puzzle on his Chelsea. As it happened, his arrival simply picked the puzzle up, shook the box around vigorously and chucked it out of the window.

Romelu Lukaku - Chelsea - 2021

After firing Inter to Serie A glory, Lukaku could only manage eight Premier League goals in 26 games and never appeared to fit into Tuchel's system, given Chelsea had found success with a mobile and interchangeable front three in the first half of 2021. A year after his signing, Lukaku was loaned back to Inter, and he will return to Chelsea for key talks with Mauricio Pochettino this summer.

4. Paul Pogba (Juventus to Man United, 2016): £93.25m

The transfer that was supposed to herald a return of the glory days to Manchester United eventually came to symbolise their decline in the post-Sir Alex Ferguson years. Pogba arrived in the same summer Jose Mourinho took the reins and that dream team would prove to be a toxic marriage.

It should be noted that when United played their best football in recent seasons, Pogba was often essential, most notably when they finished second in the Premier League under Ole Gunnar Solskjaer in 2020/21. However, none of Mourinho, Solskjaer or Ralf Rangnick could find a way to consistently prompt his best form and Pogba's woes generally coincided with long collective slumps and embarrassing defeats. After six largely unhappy years, he joined Juventus on a free transfer from United for the second time in his career.

5. Romelu Lukaku (Everton to Man United, 2017) £90m

Lukaku's second appearance on this list isn't much more pleasant. Everton received an initial £75m, with £15m more in add-ons and an ageing Wayne Rooney thrown in the bargain.

Pogba and Zlatan Ibrahimovic were the stars as United won the EFL Cup and Europa League while finishing sixth in the league in Mourinho's first season. It was hoped Lukaku would elevate them into the title picture but their eventual second-placed finish was 19 points behind City's record haul of 100. Mourinho's demise midway through the following campaign brought Solskjaer to the club and a master finisher from his playing days decided Lukaku did not figure in his plans. A return of 28 goals in 55 Premier League appearances was not appalling, but few mourned his departure.

6. Kai Havertz (Bayern Leverkusen to Chelsea, 2020): £90m

Any list like this nowadays delves into the vagaries of up-front fees, instalments and add-ons. Chelsea agreed an initial fee of £72m for Havertz, with two further chunks of £9m depending on appearances and trophies won. The German international accounted for a decent chunk of those additional payments when he scored the only goal in the 2021 Champions League final against Manchester City.

Havertz has endured a curious Chelsea career so far, including further silverware in the UEFA Super Cup and Club World Cup, but he is far from a Stamford Bridge hero. By default, he has played the majority of his football at centre-forward for a team lacking strikers, which still does not feel like a natural fit. 

As Pochettino looks to make changes to his Chelsea squad in the coming weeks, Havertz is being tracked by Mikel Arteta's Arsenal, and he could be eased out of the club for around £62m.

7. Mykhailo Mudryk (Shakhtar to Chelsea, 2023): £88.5m

Some of the transfers on the list represent presumed sure things that have yet to spark, and the lack of guarantees in Mudryk's transfer is one of the factors that makes it so intriguing.

He scored seven goals in 12 Ukrainian Premier League games this term, and three in six Champions League group outings, to underline his clear talent. But he left Shakhtar, after less than 50 appearances, for a huge fee. Mudryk does not have a wealth of senior experience to fall back on as he tries to make his way at a club that is still finding its feet under new ownership.

8. Antony (Ajax to Man United, 2022): £86m

Insofar as there's any discernible plan in Chelsea's transfer business at the moment, Mudryk represents an investment in the future. The same can be said for Brazil international Antony, who cost United a little over £1m for each of his 82 Ajax appearances.

Antony celebrates goal in 2022/23 FA Cup match vs Everton
(Getty Images)

A report by ESPN claimed United acknowledged they overpaid for a player Erik ten Hag knows well and can mould into a superstar in time. Antony has scored a few spectacular goals during his brief time at United, albeit while looking incredibly one-footed. 

9. Darwin Nunez (Benfica to Liverpool, 2022): £85m

Nunez is another player who fits the Antony and Mudryk trend of paying for potential on the back of a small sample size of impressive performances. He excelled for Benfica in 2021/22, plundering 26 Primeira Liga goals from just 24 starts and adding a further six in the Champions League. That form persuaded Liverpool to pay out an initial £64m for his services, with £21m more due in performance-related add-ons, £4.3m of which was triggered after just 10 appearances.

Darwin Nunez of Liverpool
Offside via Getty Images

Nunez's dead-eyed finishing has been shown in flashes at Anfield, sometimes in an utterly remarkable fashion. However, the 23-year-old's raw potential is there for all to see and his all-round displays can be viewed as one of the relative positives from a frustrating Liverpool season.

10. Harry Maguire (Leicester City to Man United, 2019) £80m

Six months after joining United, who upped their offer to secure Maguire amid competition from Manchester City, the England defender was named club captain. It marked an impressive start to life under Solskjaer, but the decline was stark and it is one, at club level at least, that Maguire is yet to emerge from.

Clanging mistakes from the hulking centre-back were a feature as United tanked in the late months of 2021 and Solskjaer lost his job. He remains a go-to for England boss Gareth Southgate, but despite an impressive 2022 World Cup, he remains out of ten Hag's starting plans at United.

11. Wesley Fofana (Leicester City to Chelsea, 2022): £80m

Probably the hardest man on the list to judge given his lack of action since Leicester City held firm to their Maguire benchmark and drew another astronomical fee from Chelsea.

The Blues won both Premier League games in which Fofana played, 2-1 against West Ham and Crystal Palace respectively. In between those games, Fofana's Champions League debut ended in a 1-0 defeat at Dinamo Zagreb that saw Thomas Tuchel sacked. The centre-back scored in a 3-0 win over AC Milan before being sidelined with a season ending knee injury and he now faces the challenge of re-establishing himself in a packed Chelsea squad.

MORE: Watch every Premier League match live with fuboTV in Canada

12. Virgil van Dijk (Southampton to Liverpool, 2018): £75m

Many baulked at the fee Liverpool paid Southampton for van Dijk midway through the 2017/18 season but he has proven to be transformative presence. Along with goalkeeper Alisson, who arrived the following summer, the Netherlands centre-back turned Liverpool from a thrilling but vulnerable side under Jurgen Klopp into a winning machine.

The Reds ended their 30-year wait for a 19th league title in 2019/20 and ran Manchester City devilishly close with points totals in excess of 90 in 2018/19 and 2021/22. In the former season, they won the Champions League either side of suffering heartbreak against Real Madrid in the 2018 and 2022 finals. Few of those memorable deeds would have been possible without van Dijk, the only unequivocal success on this list.

Premier League 2023/24 TV channels, live streams

Region TV Streaming
Australia — Optus Sport
Canada —

Fubo Canada
Hong Kong — Now TV
India Star Sports Disney+, Hotstar,
JioTV
Malaysia Astro SuperSport Astro Go
New Zealand Sky Sport Sky Sport Now,
Sky Go
Singapore StarHub StarHub TV+
UK Sky Sports, TNT Sports NOW TV, Sky Go,
Amazon Prime
USA USA Network,
Telemundo, Universo		 Fubo, Peacock

UK: Matches are carried across Sky Sports and TNT Sports streaming and TV platforms, with select matches on Amazon Prime.

USA: Select matches are televised on USA Network (English) and Telemundo or Universo (Spanish), and all three channels can be streamed on Fubo. The rest of the matches are streamed on NBC platform Peacock for subscribers.

Canada: Every Premier League game this season is live streamed exclusively via Fubo in Canada.

Australia: Fans in Australia can stream every match live and on demand on Optus Sport.

India: Star Sports network has the rights to show Premier League matches in India. As well as an English broadcast on Star Sports Select, select matches will be available via regional feeds on Star Sports 3 (in Bengali, English, Kannada, Malayalam), Star Sports 1 (Bangla) and Star Sports 1 (Tamil).

Dom Farrell

Dom Farrell Photo

Dom is the senior content producer for Sporting News UK. He previously worked as fan brands editor for Manchester City at Reach Plc. Prior to that, he built more than a decade of experience in the sports journalism industry, primarily for the Stats Perform and Press Association news agencies. Dom has covered major football events on location, including the entirety of Euro 2016 and the 2018 World Cup in Paris and St Petersburg respectively, along with numerous high-profile Premier League, Champions League and England international matches. Cricket and boxing are his other major sporting passions and he has covered the likes of Anthony Joshua, Tyson Fury, Wladimir Klitschko, Gennadiy Golovkin and Vasyl Lomachenko live from ringside.