10 Worst Premier League Signings In Football History (RANKED)

10 Worst Premier League Signings In Football History (RANKED)

Over the years the Premier League has seen a lot of transfers, and a lot of transfers have worked out very well, providing excellent examples of spending gone right. However, for every success there’s a failure. So, who are the 10 worst transfers to have ever happened in the top flight of English football?

[10 – Nicholas Pepe (Arsenal 2019-22)

After having an incredible season with Lille, Pepe was one of the most wanted forwards in Europe and was seen as someone who would get a move to an elite club in Europe and potentially become a world beater. So, in August of 2019, Pepe got his move to North London, becoming Arsenal’s most expensive transfer in their history. However, he just couldn’t find the same form in England, scoring 27 goals in his 112 games for the Gunners.

If this wasn’t bad enough for Arsenal, they would fail to recoup any of the £72 million spent on the Ivorian, as he left on a free in 2023. This completed the painful and hard three years in England and unfortunately landed him in 10th place as the worst Prem transfer ever.

9 – Jadon Sancho (Manchester United 2021-current)

Once the star boy of English football, Sancho was one of the best talents in Europe when United first held interest in him and in the summer of 2021 they finally landed his signature for a fee worth £73 million.

The expectations for this young man were through the roof when he joined the Red Devils; however they quickly died out after 2 seasons where he struggled to even get close to his form in Germany. The English forward didn’t reach over 10 goals in any of his seasons for United and was even exiled from the squad by both old head coach Ten Hag and current head coach Ruben Amorim. The forward has been sent on 3 loans over the last 3 seasons and is still yet to rediscover his form.

To add insult to injury for United, they thought that they had sold him after Chelsea brought him in on loan with a conditionally mandatory clause to buy him permanently; however, as a result of the wage he is on at United and a lukewarm season, Chelsea actually paid Manchester United to negate the clause in order for The Blues to not have to sign him permanently - some vote of confidence in his career.

Overall, the £73 million transfer fee and £250,000 a week in wages were not subsidised with worthy performances, and have landed him a place on this list. He's on loan at Aston Villa right now, still hoping to let that Bundesliga form show in the Premier League.

Sancho is the most disappointing signing post Fergie

https://t.co/x1Qaz67k6j

— Aidan Walsh 🔰 (@AidanWalshMUFC) August 30, 2024

**8 – Paul Pogba (Manchester United 2016-2022) **

This feels like a very familiar story for United with the French midfielder. Initially having him at the club before losing him on a free to Juventus, United bought out the wallet for one of their former youth prospects in 2016 as they forked out £90 million on the Juventus midfielder. However, this price was rarely ever justified by him.

While the first three seasons were good from the Frenchman, the next three would see him often maligned and rarely praised. Having troubles with injuries and problems with the club, the midfielder never performed at a level that warranted the price tag again. Then in 2022 the exact catalyst thing that sparked his career repeated itself: he left United on a free to Juventus.

United spent £90 million on a player who never reached the same levels that they saw in Italy, and to add onto that, a £290,000-a-week contract only for him to leave on a free (twice) – this deserves a spot on this list.

7 – Tiemoue Bakayoko (Chelsea 2017-18)

A name that some people would’ve expected to see lower in the list and the first Chelsea player to make the top 10, Bakayoko didn’t have an easy time in England after leaving Monaco. Bought by Chelsea for £40 million, they would’ve hoped for a much better player than what they ended up getting.

At the time when he joined, he was the second most expensive signing Chelsea had made, but he rarely ever looked worth the money - this was shown by his immediate departure from the club after only a single season. The ultimate end to his time at Chelsea was a game against Watford where he played a horrendous 30 minutes before seeing a red card.

6 – Angel Di Maria (Manchester United 2014-15)

One of the most talented forwards in Europe in the 2014/15 season with Real Madrid caught the eye of Manchester United, who decided to spend £60 million. However, as is often the case with big-money United signings, he struggled to adapt to the English league and failed to find his form.

After 32 games and 15 goal contributions, the Argentinian had had enough of England and looked to leave, with United agreeing to sell him. They ended up selling him to PSG for £44 million, making a £16 million loss after only 1 season. At PSG he found his form once again and put himself back as one of the best attackers in Europe.

5 – Mykhaylo Mudryk (Chelsea 2022-current)

At the peak of his powers, Mudryk was one of the most exciting attackers in Europe, and a player other top clubs like Arsenal were after; it was his clear elite talent that made Chelsea push through and land the winger’s signature. But hindsight is a wonderful thing, and now, every Chelsea fan will tell you the move was a mistake - his time on the pitch at Stamford Bridge was supremely underwhelming, as he scored 10 goals and created 8 in 73 games.

While these aren’t bad numbers for a young player who is playing for the first time in a top 5 league, the price tag meant expectations were much higher. The fee was £62 million and could’ve reached £90 million had various add-ons been met. However, this extra fee doesn’t look like it will ever be paid, as he has now been banned from football due to the use of a performance-enhancing drug. With the ban expected to be similar to Pogba’s 4 years, Mudryk's price, performances and now the ban definitely warrant him a place on the list.

Mykhailo Mudryk being signed for £88.5 million is one of the worst transfers of all time

https://t.co/RhcbbCTgcV

— Out of Context Football Manager (@nocontextfm1) December 16, 2023

4 – Alexis Sanchez (Manchester United 2018-19)

Once again, another United signing on the list, and once again a forward who was an elite player before joining them. Sanchez joined United from Arsenal in January 2018, as he wanted to join a club with a better chance of winning trophies; Arsenal was never going to fulfil his ambitions on that front.

However, he never managed to find his form at the Red Devils. In the one and a half seasons he was there, he played 45 games, contributing to 14 goals. These are far from the figures you would’ve expected from a forward who had just got 45 goal contributions with Arsenal the season prior. While the transfer by itself was bad enough, the wages are what made this transfer so painful for United, as once again they see a player put on a massive wage, paying Sanchez £360,000 a week.

3 – Antony (Manchester United 2022-2024)

The latest marquee signing to join Manchester United and, overall, one of the worst in their history. The Brazilian started his career off at United very well, scoring in his first three games and playing well; however, his form quickly nosedived. 17 goal contributions in 3 seasons for United is not good enough for any player, let alone a player who cost them £86 million.

The Brazilian was very quickly pounced on by the English media, who were very quick to pick up on his poor performance, and it was clear he felt the pressure. After his 1st season, he only got 6 more goal contributions in 52 matches. These numbers were the final straw, and similar to Di Maria, he left and found his form again this time at Real Betis, who paid £21.5 million for him. Overall, United lost a lot of money in this transfer and didn’t perform well enough for it to be worth it.

2 – Danny Drinkwater (Chelsea 2017-2022)

£35 million for him. After Leicester City won the league title, Chelsea spent £35 million on the midfielder, and it proved to be one of the worst in Premier League history. He never found his form again after that season and struggled to ever get into the Chelsea first team; overall, he played 23 games for Chelsea and scored a single goal, which, in his defence, was a belter against Stoke. Chelsea spent well over a million a game for the player who was on a 5-year contract, 80% of which he spent on loan. Very much one of the worst transfers, not just in the Prem but ever.

1 – Romelu Lukaku (Chelsea 2021-2022)

The worst transfer in Premier League history, and it’s a Chelsea striker, to the shock of absolutely no one. Chelsea is known as a striker graveyard; however, when they announced the signing of Lukaku after winning the Champions League, many people thought they had finally found a solution.

That was not the case. After just four months at the club, everything fell apart for him and Chelsea as an interview dropped about him missing and wanting to go back to Inter Milan. This destroyed his relationship with the club and fans. The striker who cost Chelsea £97.5 million was cast out of the team and left in the summer. He is comfortably the worst transfer in the history of the league with his combined cost and wages, with Chelsea also struggling to sell him after he broke bridges at Inter Milan.

What do you think? Who is the worst transfer in the history of the Premier League?