Transfer Window: Biggest deals in Premier League history

With the start of the new Premier League season fast approaching, clubs in the English top flight are working hard to complete their transfer business. 

Clubs including Arsenal, Chelsea and Manchester United have already delved into the market for new signings, but what are the most expensive transfers in Premier League history? Here, we take a look at the top five.

5. Romelu Lukaku – Inter Milan to Chelsea (£97.5 million)

Lukaku rejoined Chelsea in 2021, having scored 24 goals for Inter Milan as they won the Serie A title the previous season. The Belgian, who had initially departed Stamford Bridge in 2014, but endured a difficult return to West London. The Belgian striker scored just 15 goals across all competitions during the 2021/22 campaign, and was then loaned back to Inter ahead of the following campaign. He spent last term on loan at Roma, and has been linked with Italian side Napoli in recent days.

Lukaku endured a frustrating return to Chelsea in 2021

4. Jack Grealish – Aston Villa to Manchester City (£100 million)

Boyhood Villa fan Grealish had established himself as a cult hero at Villa Park, before departing to join Pep Guardiola’s side in 2021, for what was a Premier League record at the time. The England international has since enjoyed staggering success at The Etihad, winning the treble in 2023, before retaining the Premier League title last term. Grealish has a combined 32 goals and assists in 125 games for the Citizens across all competitions.

Grealish is the most expensive English player of all time

3. Declan Rice – West Ham United to Arsenal (£105 million)

In his final game for the Hammers, Rice lifted the Europa Conference League trophy after victory over Italian outfit Fiorentina. The midfielder, who is a regular for England, enjoyed an impressive debut season at The Emirates after making the move across London last summer. He played in all 38 of Arsenal’s league games last season, scoring seven goals and registering nine assists.

Rice played in every Premier League game during his first season with Arsenal

2. Enzo Fernandez – Benfica to Chelsea (£106.8 million)

Argentine midfielder Fernandez became the most expensive signing in Premier League history when he moved from Benfica to Chelsea in January 2023, a year after winning the World Cup. The 23-year-old enjoyed a positive second half of the 2022/23 campaign, and continued his development last term until he was forced to undergo groin surgery, ruling him out for Chelsea’s final six league games.

Fernandez was the most expensive player in Premier League history when he joined Chelsea in 2023

1. Moises Caicedo – Brighton & Hove Albion to Chelsea (£115 million)

Despite already boasting the Premier League’s most expensive ever player in midfield, Chelsea decided they needed further reinforcements in the middle of the park last summer and duly added Caicedo to their ranks, for a record fee. The Ecuador international endured a nightmare debut for the Blues, giving away a penalty after being substituted on during a defeat against London rivals West Ham United, but he finished the season strongly and scored his first goal for the club – in some style – on the final day of last term.

Caicedo is currently the most expensive player in Premier League history