Top six transfer deadline day signings that flopped ft. Nunes & Antony

Even giants like Manchester United, Chelsea and Liverpool have got their deadline day signings wrong!

From blockbuster fees to surprise moves, several high-profile players have changed clubs in deals that generated enormous excitement and expectations.

The transfers often looked logical at the time, but they don’t work out as they should have. Transfer deadline day, especially in the summer transfer window, is one of the most unpredictable occasions in the world of football. The clubs battle it out against the clock to complete deals. Some late moves become masterstrokes, and others are remembered as costly errors.

Names that became expensive mistakes include Antony, Alexander Isak, Fernando Torres, Danny Drinkwater, Matheus Nunes and Michael Owen. For some reason, several deadline day signings have failed to live up to the expectations surrounding them.

Also Read: Top 10 most expensive transfers of summer 2026 ft. Marc Cucurella & Elliot Anderson

Flopped transfer deadline day signings

7. Michael Owen

From Liverpool, Michael Owen signed for the Spanish giants, Real Madrid, in 2004, to improve his chances of getting selected for the 2006 World Cup squad. He returned to England a year later on deadline day in search of more time on the field and joined Newcastle United in the summer of 2005 for a fee of £16.8m.

Due to a string of injuries, Owen was seen for a limited time on the field for the Magpies. He was ultimately selected for the World Cup, but suffered an ACL injury which kept him out till April 2007.

6. Danny Drinkwater

Danny Drinkwater shuffled between many clubs before signing for Leicester City in 2012. The English midfielder stayed there for five years, and then Chelsea came knocking in the summer of 2017, with a deadline-day move, after he won the Premier League title with the Foxes. The Blues locked in a deal for £35 million.

During his first season with Chelsea, Drinkwater only made 22 appearances due to injuries. He was not in plans for Maurizio Sarri during his second season with the club and failed to make any Premier League appearances for the club.

5. Andy Carroll

After Fernando Torres left the club in 2011, Liverpool were desperately looking for a centre-forward. The Reds spent £35 million and signed Andy Carroll from the fellow English top-division club, Newcastle United. This fee also became a record for a British player at the time, that too on the transfer deadline day.

Andy Carroll became the first-choice striker for Liverpool, but quite literally failed to deliver. His first goal for the Reds came after four months and is considered a flop move.

4. Fernando Torres

For £50m, Chelsea completed the shocking deadline-day transfer of Fernando Torres from Liverpool in 2011. It was a really controversial move halfway through the 2010-11 campaign. The Spanish star was considered a world-class forward at that time, but it did not work out for either the player or the club.

Torres only managed to score one goal during the remainder of the season. There was also a 24-game goal drought during his debut campaign at Stamford Bridge.

3. Matheus Nunes

The Portuguese star was originally a midfielder and spent most of the time of his career in his native country before his move to Wolverhampton Wanderers in 2022. Just a year later, Manchester City came knocking and spent £53m to sign Matheus Nunes on deadline day. They signed him to replace Ilkay Gundogan, but it did not quite work for them.

Nunes has not had enough playing time on his resume with Man City since then and has now transitioned into a full-back.

2. Antony

After his performances and presence on the field for AFC Ajax, the Premier League giants, Manchester United, decided to sign the Brazilian forward in 2022. It was a hefty £85 million move, which only got worse with time.

His start at Old Trafford was perfect. Antony scored a goal on his debut, but failed to impress during the rest of the season. He received criticism from fans for his attitude on the pitch and his lack of ability. The Brazilian ultimately moved to LaLiga after signing for Real Betis in 2025.

1. Alexander Isak

Alexander Isak came up with stunning performances for Newcastle United during the 2024-25 campaign. He scored 23 goals in 34 Premier League appearances and had six assists to his name. It was enough to attract Liverpool.

The Reds signed him for a whopping £125m transfer fee in 2025. For the price, Isak’s performances were nowhere near what they should’ve been. He suffered a major injury during the same year in December. The Swedish player has failed to find his form since then and is still a part of the club.

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