Ranking the 20 most expensive Premier League signings from worst to best | OneFootball

In one of the most bizarre transfer sagas the Premier League has ever seen, Moises Caicedo is set to make a move to Chelsea.

The Ecuadorian has found himself stuck in the middle of a tug-of-war between the Blues and Liverpool, with the latter initially agreeing a record-breaking fee. However, after telling Liverpool that his preference was a move to Stamford Bridge, the west London club have now agreed a move for the midfielder.

Fabrizio Romano confirmed that the five-time Premier League champions had agreed a deal with Brighton worth £115 million, meaning that Caicedo will overtake one of his new teammates as the most expensive signing ever made by a Premier League club.

More and more money is being invested into transfers in English football's top flight meaning numbers will continue to get even more ridiculous, with all the biggest moves in history being made in the last few years for the most part.

But money does not always guarantee success, and there have been plenty of players who made big money moves, only to flop at their new clubs. So, with Caicedo set to be the latest player to move for a huge fee, the team at GIVEMESPORT thought we would rank the 20 most expensive Premier League signings from worst to best.

Now, this list is highly subjective, and there will certainly be those of you who disagree with our ranking. If you would make any changes, feel free to let us know in our social media comments. But without further ado, here is how we would rank the 20 most expensive players in English football.

20 Romelu Lukaku - Inter Milan to Chelsea (€113 million)

We're starting off with one of the worst transfers in Premier League history and one of two Lukaku entries on this list. The striker returned to Chelsea after he failed to make it into the first-team during his first stint at the club. An ill-informed decision to say he was hopeful of a return to Inter Milan was the beginning of the end for the Belgian, who had failed to find his best form until that point.

19 Kepa Arrizabalaga - Athletic Bilbao to Chelsea (€80 million)

The most expensive goalkeeper in world football is being sent out on loan as we speak. Kepa's time at Stamford Bridge has been underwhelming to say the least. Supporters had hoped the void left by Thibaut Courtois' move to Madrid would be easily filled by the former Bilbao man. That has not been the case as too many errors in between the posts have meant the club are willing to loan him out.

18 Nicolas Pepe - Lille to Arsenal (€80 million)

Big things were expected of the tricky Ivorian when he made the move from Ligue 1 to the Premier League in 2019. Fast forward four seasons, and the winger has just finished a loan spell back in France with no way back into the Arsenal first-team plans. Bukayo Saka has gone on to become the star on the right-wing that fans had hoped Pepe would.

17 Romelu Lukaku - Everton to Manchester United (€84.7 million)

Man United believed they had bagged their striker for the next decade when they wrapped up the deal to bring Lukaku to the 'Theatre of Dreams'. The big centre-forward did not have the impact expected as he never really clicked in the side. His move was ultimately a misguided one, and concluded with a move to Inter Milan where he re-captured his best form.

16 Ángel Di María - Real Madrid to Manchester United (€75 million)

Man United fans thought they had pulled off the deal of the 2014 summer transfer window when Real Madrid parted ways with the Argentine winger after four successful years at the Spanish club. He had only just helped Los Blancos win the Champions League at the end of the previous campaign with a man of the match perfromance against fierce rivals, Atletico Madrid. Di Maria started his time in England with some impressive displays that made the deal look like it could not fail, however that form did not last long and injury issues began to hold him back.

15 Jadon Sancho - Borussia Dortmund to Manchester United (€85 million)

Yet another transfer that has still not worked out fully, the English winger has flattered to deceive for the majority of his time in the Premier League. He missed a large portion of last season due to personal issues and did not set the world alight upon his return. 2023/24 will be a crucial year for him.

14 Kai Havertz - Bayer Leverkusen to Chelsea (€80 million)

Chelsea parted company with Havertz this summer after a largely disapppointing three seasons. 19 goals in over 90 appearances is nowhere near good enough for a player that led the line for the majority of his spell at the club. One of those goals did win the Blues a Champions League title, mind you.

13 Harry Maguire - Leicester City to Manchester United (€87 million)

Six months into Maguire's career at Old Trafford, he was handed the captain's armband and things looked to go downhill from that point forward. Mistakes and loss of confidence have contributed to his loss of a starting berth and even his captaincy in recent weeks. A move away from the club looks a likely outcome this summer.

12 Kai Havertz - Chelsea to Arsenal (€75 million)

The German made an unexpected move across London to join Mikel Arteta's title-hopeful Arsenal side. The Gunners had a strong 2022/23 season as they pushed Manchester City all the way in the title race, but ultimately came up short. Havertz has famously struggled to score enough goals when played as a centre forward, although he looks set to be given a new role for his new club.

11 Rasmus Hojlund - Atalanta to Manchester United (€75 million)

United's latest signing becomes one of the 20 most expensive Premier League transfers of all-time. The Danish striker has enjoyed a strong European Championship qualifying campaign for his national team with six goals in four games. He did, however, only manage to bag nine goals in Serie A last season despite catching the eye of many. Time will tell if this was a good use of funds with the Red Devils in desperate need of a consistent figure to lead the line.

10 Darwin Nunez - Benfica to Liverpool (€80 million)

A chaotic first year at Anfield is in the bag for the Uruguayan striker, with 14 goals in all competitions under his belt despite a lack of confidence in front of goal at times. His transfer fee is yet to be justified but his manager - Jurgen Klopp - continues to show faith in Liverpool's new number nine.

9 Paul Pogba - Juventus to Manchester United (€105 million)

The former youth product returned to United only a few years after he was allowed to leave on a free transfer. Pogba did have moments of brilliance back in Manchester, with 90 goal contributions in 233 games for the Red Devils. But ultimately, the World Cup winning midfielder didn't live up to expectations after coming back from Italy as disappointing performances and injuries have led to a second free transfer to Juve.

8 Wesley Fofana - Leicester City to Chelsea (€80.4 million)

Fofana made the move to Chelsea with a lot of potential to be one of the top defenders in the country, but two massive injuries have halted any progress. Missing the majority of his debut season with the club, the French centre-back was hoping to get back to his best in 2023/24 before suffering another long-term injury.

7 Antony - Ajax to Manchester United (€95 million)

United make yet another appearance on this list, showcasing the vasts amount of money they have spent in recent times in search of a first league title in a decade. 4 league goals in Antony's opening campaign at the club is not the best introduction to his new fan base, but his second year will be more telling.

6 Josko Gvardiol - RB Leipzig to Manchester City (€90 million)

The newest addition to the list until Caicedo's move is confirmed, Gvardiol made his debut as a substitute against Burnley. At 21-years-old, the Croatian defender will be a key figure in the defence of the club for the next decade if all goes to plan. Fans of English football will get more familiar with his game as the season goes on.

5 Declan Rice - West Ham to Arsenal (€116.6 million)

Rice has made his long-awaited Arsenal debut after sealing a European trophy with West Ham in his final game for the club. The Gunners fought off competition from last season's league winner to secure the English defensive midfielder, and he is seen as the man to push them from title contenders to title winners.

4 Enzo Fernandez - Benfica to Chelsea (€121 million)

Set to be overtaken by the enormous fee that will see Caicedo become his teammate, Fernandez only held the record as most expensive transfer to a Premier League club for six months. Chelsea will have spent over €200 million on their midfield duo in less than a year. The 2022 World Cup winner is expected to come into his own in the very near future.

3 Jack Grealish - Aston Villa to Manchester City (€117.5 million)

Currently the second most expensive signing made by a top flight side, Grealish moved for a record fee at the time from his boyhood club to Man City. His choice has paid off with two league titles under his belt inside as many years. Former Villa star, Grealish, has had a summer full of partying as he played a big part in his team's treble winning exploits.

2 Virgil van Dijk - Southampton to Liverpool (€84.65 million)

The Dutchman had a truly transfromational impact almost instantly after moving to Liverpool in January 2018. Klopp was willing to wait to get his man after missing out in the summer window, and that decision has been fully vindicated as Van Dijk is now the club captain after winning all the big prizes.

1 Kevin de Bruyne - Wolfsburg to Man City (€76 million)

Even for such a large sum of money, there can be no argument that the Belgian has been more than worth his transfer fee for the Citizens. Five Premier League titles, one Champions League success and a barrell full of domestic cups are all firmly cemented on his ever-growing CV.