Top 10 Worst Transfers In Football History (All Times) | Updated 2022

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Football transfers and deal signings always thrill the fans and every football feels excited about the new outcomes of the game. Team Management always wants to sign the best players by offering them the highest salaries and long-time work.

However, sometimes these transfers and signing deals do not go as planned due to the poor performances of the players, their injuries, or bad team management.

Even the players with the highest salaries turnout to be the worst sign. So, here we have made the list of Top 10 Worst Transfers in Football history. You can go through the list to know which is the worst transfer of all times in football history.

Top 10 Worst Transfers In Football History

Some players could not live up to the expectations of their fans when they are transferred from one club to another. Injuries, Mishandling, and other factors turn their transfers into a flop. Here is the list of Top 10 Worst Transfers in Football History.

Player Name Transfer Price Transfer
Alexis Sanchez £18.2 million Arsenal To Manchester united
Andy Caroll £35 million Newcastle to Liverpool
Fernando Torres £50 million Liverpool to Chelsea
Andriy Shevchenko £30.8 million Milan to Chelsea
Jackson Martinez €35 million Porto to Atletico Madrid
Gaizka Mendieta €47.7 million Valencia to Lazio
Angel di Maria £59.7 million Real Madrid to Manchester United
Roberto Soldado £26 million Valencia to Tottenham
Christian Benteke £32.5 million Aston Villa to Liverpool
Jonathan Woodgate £13.4 million Newcastle to Real Madrid

1. Alexis Sánchez

  • Transfer: Arsenal to Manchester United
  • Transfer Value: 18.2 million GBP

Chilean professional footballer Alexis Sanchez Transfering to Manchester United on 29 August 2019 in a swapping deal for Henrikh Mkhitaryan with Arsenal is considered to be the Worst Transfer in the history of football history. Soon after Sanchez moved to Arsenal, his fantastic form started to decline. Perhaps, Manchester United bet on the wrong horse and did not get the results they wanted.

He managed to score only five goals in two and a half years for Manchester United. This stands as a terrible signing for any attacking forward. Alexis Sanchez received the highest salary from Woodward but could not perform with the Club. This ultimately led to his transfer from Manchester United to Inter Milan forming the basis of David de Gea’s bumper contract.

Chile’s all-time top scorer was not a bad choice for Manchester United at the time of signing. It’s just that, Sanchez lost his form during his time with the Club. Surprisingly, United’s CEO Woodward could not back from the deal and it became ridiculous with Sanchez numbers.

2. Andy Carroll

  • Transfer: Newcastle to Liverpool
  • Transfer Value: £35 million

Liverpool signing Andy Carroll on 31st January 2011 rates as the 2nd worst transfer in the history of football. Caroll calls back his transfer stating ” I was 22 when I moved. I couldn’t handle Liverpool at the time”. He also stated that he had to google his Liver Pool teammates at the helicopter ride because he knew nothing about them at that time.

This poor decision of Liver Pool buying Andy Caroll hurt the club and Andy Caroll a lot. This is also rated as the 2nd worst transfer in football history. Caroll was severely injured soon after joining the club, therefore he could not provide solid support to the Liverpool attacking power. His transfer became the unavoidable truth for Liverpool.

Andy Caroll managed to score only 6 goals in three seasons of Premier League and his transfer resulted in a huge amount of money waste for Liverpool.

3. Fernando Torres

  • Transfer: Liverpool to Chelsea
  • Transfer Value: £50 million

Former Spanish Footballer Fernando Torres was transferred to Chelsa by Liverpool for the cost of 50 million pounds on 31st January 2011. This is said to be the 3rd worst Transfer in the history of football. Torres failed to impress football fans with his performance at Chelsea for which he got famous during his time at Liverpool. Moreover, it also weighed down the Chelsea bid in the hope for Torres to become the leading striker for the club.

The huge amount of the signing contract and Fernando Torres previous performances made a lot of impact on the football fans. However, it later turned out to be a failed transfer. Despite the outcomes, Fernando Torres was the first player in football history to be loaned by another team.

In a surprising move, Chelsea brought back their leading goalscorer Drogba, who had scored 20 goals in Premier League for Chelsea in the previous seasons.

4. Andriy Shevchenko

  • Transfer: Milan to Chelsea
  • Transfer Value: £30.8 million

Former Ukrainian Footballer and current football manager Andriy Shevchenko grabs the 4th spot on our list. He left Milan to join Chelsea on 28 May 2006 for the cost of £30.8 million. This was the highest price for an English Payer to be signed by any club. However, the later outcome was not the favor for which Roman Abramovich paid.

Many Chelsea fans criticized Abramovich for the hasty deal to sign the 30 years old striker for the club. Later, it turned out that Andriy Shevchenko was not the effective striker that he used to be in the past. Nevertheless, This costly transfer still qualifies to make it on our list.

After struggling to make an impression at Chelsea, Andriy Shevchenko finally returned to his home club Milan on loan.

5. Jackson Martinez

  • Transfer: Porto to Atletico Madrid
  • Transfer Value: €35 million

Colombian former professional footballer Jackson Martinez takes the 5th spot on our list. After playing for three seasons for Porto, Atletico Madrid purchased him for the cost of €35 million. However, during his time at Atletico Madrid, he struggled to score goals, and later he was struck with an ankle injury during a match that ruled him out for a month.

Jackson Martinez’s transfer turned out to be a failure for the club. The press stated him as a flop and Atletico Madrid’s president Enrique Cerezo said that He was not at the level of the Club. He managed to score three goals in 22 appearances for the club. A year later, Martinez was offered €42m to play for Guangzhou Evergrande in the Chinese Super League.

Nevertheless, Jackson Martinez’s Transfer to Atletico Madrid is considered one of the worst transfers in football history.

6. Gaizka Mendieta

  • Transfer: Valencia to Lazio
  • Transfer Value: €47.7 million

Spanish Former Professional Footballer Gazika Mendieta joins our list at the 6th spot. His Transfer from Valencia to the Lazio for a massive amount of 47.7 million is considered as one of the worst transfers in the history of football. Though Gaizka won the  “European Midfielder of the Season” and “UEFA Best Midfielder of the Year” awards during his time at Valencia, he struggled to find his feet at the Lazio.

Gazika Mendita Transfer to Lazio made him the sixth expensive player of all time in football. However, his performances in Serie A were disappointing to the fans. Despite paying for one of the best midfielders at the time, Lazio could not find support from Mendieta which makes him one of the worst transfers of all time.

Regarded as one of the best midfielders of all time, Gaizka Mendieta earns his name on our list of worst transfers in football history.

7. Angel Di Maria

  • Transfer: Real Madrid to Manchester United
  • Transfer Value: £59.7 million

Argentine Professional Footballer Angel Di Maria also put together on our list at the 7th spot. His transfer from Real Madrid to Manchester United for a transfer fee of  £59.7 million is considered as one of the worst transfers in the history of football. His transfer deal from Real Madrid to Manchester United is regarded as one of the most expensive transfers of all time and the highest transfer fee paid by an English Club at the time.

Di Maria began the season on a high note and won the players of the month award. Sky Sports highlighted his performance by Stating ” Player Cam Feature”. However, he was struck with a Hamstring injury during the United vs Hull City match after that he struggled to score goals for the club.

On 9th March 2015, United sent off Angel Di Maria as he was booked for diving and for grabbing the shirt of the referee. At the end of the season, The Daily Graph labeled his transfer as the worst signing of the season. Thus, he makes it on our list at the 7th spot.

8. Roberto Soldado

  • Transfer: Valencia to Tottenham
  • Transfer Value: £26 million

Spanish Professional Footballer Roberto Soldado also makes it on our list at the 8t spot. His transfer from Tottenham Hostpur to Valencia for the price of £26 million broke the Club’s previous record of most expensive bid, is also regarded as one of the worst transfers of all times in the history of football.

Valencia fans had the highest hope from Soldado and the hefty price that was paid for his transfer. However, their hopes were shattered when Roberto Soldado could perform as per the expectations.

Soldado netted just six times only two of which came from open play in his debut season. He was included in The Telegraph’s list of 10 worst buys of the Premier Leauge Season. Therefore, Roberto Soldado also earns his name on our list of worst transfers of all time in football.

9. Christian Benteke

  • Transfer: Aston Villa to Liverpool
  • Transfer Value: £32.5 million

Belgian Professional Footballer Christian Benteke also puts together in our list at the 9th spot. His transfer from Aston Villa to Liverpool for the release price of  £32.5 million is considered as one of the worst transfers of all time in football. This transfer was rated as the second most expensive transfer ever in football.

His excellent performances at the Aston Villa made a great impact on Liverpool Authorities. His initial days at the club were superb and he lead the club to victory many times. However, he had to miss many games for the club to his injuries. Later, he was also found on the bench due to him not fitting into  Jürgen Klopp’s style of play.

All these circumstances led Christian Benteke to end his stint with the club after making 42 appearances and scoring 10 goals. Therefore, Benteke earns his name to be on our list of worst transfers of all time.

10. Jonathan Woodgate

  • Transfer: Newcastle to Real Madrid
  • Transfer Value: £13.4 million

Finally, English Former Footballer Jonathan Woodgate makes the last spot on our list. His transfer from Newcastle United to Real Madrid for the transfer fee of £13.4 million is considered the worst transfer of all time. Many footballs fans were shocked to see the transfer as Woodgate carried a bad reputation of injuries with his previous clubs. More Surprisingly, Jonathan Woodgate also was injured at the time of the transfer.

He did make appearances for Real Madrid in the first season due to his injuries. He scored his own goal during a league match against Athletic Bilbao and was later sent off for a second bookable offense. Furthermore, injuries stopped him from playing any more games for the club and he could not make it to England’s squad for FIFA World Cup 2006.

Jonathan Woodgate was voted as the worst signing of the 21st century by Users of Spain’s Website Marca. Therefore, He earns his name on our list of the worst signing of all time.

FAQs – Frequently Asked Questions

What are the top 5 worst transfers in football history?

Alexis Sanchez (Arsenal to Manchester United), Andy Carroll (Newcastle to Liverpool), Fernando Torres (Liverpool to Chelsea), Andriy Shevchenko (Milan to Chelsea), Jackson Martinez (Porto to Atletico) are the top 5 worst transfers in the history of football.

Who is the worst transfer in football history?

Alexis Sanchez Transfer from Arsenal to Manchester United is considered as the worst Transfer in football history. United paid a huge amount of money for the transfer but could not get expected results from Sanchez.

Who is the biggest football flop?

Jackson Martinez’s Transfer from Porto to Atletico Madrid for the price of €35 million is the biggest football flop. He could not perform for Atletico Madrid and Club lost a huge amount of money in the transfer.

What are the latest worst transfers in football?

The list of latest Worst Transfers in football includes Antoine Griezmann ( Atletico Madrid to Barcelona in 2021), Eden Hazard (Chelsea to Real Madrid in 2019), Philippe Coutinho (Liverpool to Barcelona in 2018), and Ousmane Dembele (Borussia Dortmund to Barcelona in 2017).

Conclusion

So here is our list. Who do you think should be on our list? Let us know in the comment box.