What Are Some of the Worst Football Transfers?

Transfers in football are always an exciting ordeal as it means a fresh addition to a team’s lineup and gameplay. One new player can always make or break a game’s match, after all. Sports enthusiasts and bettors always keep an eye out for soccer transfer news because of the impact of every player in every team. Plus, it’s always interesting how one person can interact with already established members of a football team.


However, a football player transfer doesn’t always turn out as beneficial as anyone wants it to be. Sometimes, a transfer could be seen as a mistake. A change in a team is always a gamble. Things can get better or worse, depending on who the subject of the deal is, whether it be due to low performance, unforeseen injuries, or difficulties with the management itself. In this article, we’ll be showcasing a list of the worst transfers in football that changed a team’s outlook for the worst.

Christian Benteke


Christian Benteke transferred from Aston Villa to Liverpool for the price of £32.5 million.

This move was motivated by his excellent performance as a striker at Aston Villa, which Liverpool had the keenness to see, hence the signing of the transfer. The main problem the transfer presented was the misalignment of the striker’s expectation with Liverpool’s plans for the role he was to take. In the end, the transfer proved to be less fruitful than what the teams hoped it would be.


Danny Drinkwater

Danny Drinkwater signed from Leicester to Chelsea in 2017, and sadly, he did not prove to be worth the money as he only appeared in 12 Premier League appearances and not much else. Chelsea signed the deal for £34.1 million, a hefty sum for someone who remained unused in the games throughout the season.


Drinkwater was also loaned to Burnley and Aston Villa, but such moves proved to be worse than his stint in Chelsea. The midfielder was involved in an altercation with a teammate in training as well as in a fight in a nightclub after he allegedly attempted to bring home Kgosi Ntlhe’s girlfriend/ With Burnley, he only made one appearance, and four with Aston Villa, but he shortly sent back to Chelsea after the training altercation.

Edgar Davids


In 2006, Spurs player transferred player Edgar Davids had a player transfer set up with Greek club AEK Athens, which would have given both clubs a massive profit on their investment in player transfers. But because of a late player transfer application submitted to FIFA by the UEFA, player transfers in Europe were frozen until January 2007, so any agreed-upon player transfers couldn’t be completed before new year’s day.

Davids played for Spurs throughout December, but when he found out about player transfers being frozen, he decided to run away from his player transfer contract. The player eventually came back and accepted player transfers to AEK Athens in January 2007 after player transfers had been reopened.

Branislav Ivanovic

Branislav Ivanovic was transferred for €22 million, which at the time was considered to be a very high player transfer fee because of the economic crisis that had hit many countries around 2008-2009.

Rumours have it that his former club wanted to sell him for a cheaper player transfer fee but ended up accepting the player’s demands because they didn’t want their player going to one of their direct rivals for a reduced price.

After arriving at his new club, player transfers in Branislav Ivanovic’s player contract caused all sorts of player transfer problems for the player. He ended up getting injured and unable to play for months after his player transfer, which prompted rumours linking him to several clubs around Europe.

Marc Batra

Marc Batra is another player who never got to play a game with his current club because he refused to honour his former club’s player transfer contract. The attacking midfielder had agreed on transfer terms to join American MLS side FC Dallas back in 2008 but later changed his mind because he wanted more money than what was offered by the MLS side.

Despite the fact that FCD tried loaning Batra to other player transfers in Europe, Barcelona refused to sell player Batra for less than the player’s transfer fee. So FCD ended up having to re-work Batra’s transfer contract because of this fact until player transfers allowed him to go on loan with the U.S side.

Mario Jardel

Galatasaray sporting director Adnan Sezgin Yıldırım stated how he was happy with his club’s player transfer dealings during the winter 2013-2014 player transfer window. But looking back now, it seems that he may have been mistaken about one of his additions during that time period.

Mario Jardel transferred to Galatasaray via the player’s representative. The player performed well during the pre-season and in friendlies with the Turkish giant, but his performance in official matches was so poor that he eventually ended up getting cut in early 2014 after only making one appearance for player transfers. No club has signed the player since then, and it looks like Mario Jardel’s poor spell at Gala will be just another addition to his already long list of unsuccessful stints.

Jonathan Woodgate

Jonathan Woodgate transferred from Newcastle to Madrid with a £13.4 million contract signed. He stayed for 14 months with the prestigious club, but his opportunities were sadly cut short as he transferred with an injury.

His very first appearance for Real ended badly as he scored an own goal against Club Athletic, and he was later shown a yellow card. Consequently, he was dismissed from Real Madrid.

Fernando Torres

One player transfer that stands out and is considered by many as one of the worst player transfers in history was when Fernando Torres joined Chelsea from Liverpool on January 31st, 2011for £50 million ($71 million). The player had just come off an impressive World Cup with Spain where he scored a goal for his country in the finals against the Netherlands.

On paper, Chelsea’s player transfer seemed great since they were acquiring one of Europe’s best strikers at that time, but that player transfer turned out to be a nightmare for them. Torres failed to shine under then-manager Carlo Ancelotti and was often on the bench as a substitute player. When Ancelotti was dismissed and replaced by Andre Villas-Boas, Torres saw himself demoted even further down on the pecking order and wanted out — which led him to join AC Milan on loan during this past January transfer window.

Denílson de Oliveira

Denilson was one of the best central midfielders in world football during his time with the Brazilian club Sao Paulo, where he won several Player of the Year awards and Player of the Tournament awards at both international and domestic level matches. Real Madrid player Jorge Valdivia was initially supposed to join Real Betis on loan from player transfer giant Paris Saint-Germain, but due to an injury clause, Jorge Valdivia refused to go on loan to player transfer rival Real Betis.

Real Betis had no choice but to recruit another player after their player transfer budget was circumventedValdivia’s refusal. Denilson’s player transfer fee was approximately €12 million ($15 million) for him to play at Real Betis during the 2012-13 season. However, his career there turned out to be an absolute nightmare as he couldn’t score once or even see his name printed in the starting 11. Thankfully for him, then manager Juan Carlos Oltra made sure that Denilson would get some playing time during each game regardless of how ineffective he was because not playing him would have meant that player transfer money would be completely wasted.

Francis Jeffers

Player transfer fees and salaries became so inflated during the height of global football player transfer that clubs in world football were forced to spend big on players just so they could keep up. One such example is English striker Francis Jeffers joining Arsenal from player transfer rival Everton for a club-record fee of €4.6 million ($5.7 million).

Arsenal manager Arsene Wenger was so impressed with Jeffers’ goal-scoring abilities during his days at Everton that he decided to break the club transfer fee by signing him up even though he only scored 20 goals in over 100 appearances for Everton.

The worst part about it is that Francis Jeffers didn’t live up to expectations and went from being one of English football’s brightest young stars to a flop within a matter of months. Just three years after joining Arsenal, Jeffers transferred back to his old club Everton because within three years after joining, he didn’t score a single goal in the player transfer period.

Andriy Shevchenko

Jose Mourinho didn’t realise that when you spend big on players, it doesn’t necessarily mean you’ll get the results that you want, especially if they’re past their prime and don’t have what it takes to perform at such a high level anymore. This was exactly the case when he decided to sign Ukrainian striker Andriy Shevchenko from AC Milan for a massive €30 million ($35.25 million).

Mourinho had also paid big time when he lured French midfielder Claude Makelele from Real Madrid. But the worst part is that the Portuguese manager didn’t even get what he wanted out of both deals because Makelele was already past his prime while Shevchenko’s best years were behind him by the time he joined Chelsea.

Andy Carroll

When it comes to football, there’s no bigger waste of money than what English club Liverpool did in January 2011 by paying big for English striker Andy Carroll from rival Newcastle United. To make matters worse, they paid a whopping €42 million ($49.4 million), which was a British and European Union (EU) national and regional record at that time.

Liverpool already had England international striker Fernando Torres on its payroll, and the worst part about it all is that Carroll was unfit to play with Torres because he had a history of injuries even at his old club Newcastle where they suffered several injuries during his short stint with the team. Carroll spent most of his time on injury and didn’t score any single goal in half a season before transferring back to player transfer rival West Ham United.

Boško Balaban

Boško Balaban was signed from Dinamo Zagreb of Croatia for £7 million back in 2001. The Croatian player had no significant performances or games for eight straight months when he transferred to Aston Villa until that one game when he barely reached 140 minutes within eight appearances, and in none of those performances did he score a single goal.

Angel Di Maria

Angel Di Maria’s run with Manchester United was a slow and steep descent into one of the worst transfers in football history. Di Maria started out strong, winning Goal and Player of the Month, at the beginning of the season.

He had just transferred from Real Madrid to Manchester United for £59.7 million, but all that money went to waste after a problem with his hamstring. The pre-season trip to America where he missed his medical in Paris further worsened Di Maria’s footing in football transfer history.

Dani Osvaldo

Dani Osvaldo has one of the most controversial careers in football history with the number of borderline insane antics he did in the course of his career. While playing for Roma, he punched Argentine midfielder Erik Lamela for not passing to him in their 2011 defeat to Udinese.

What eventually pushed him to retirement was after he headbutted Southampton’s team captain Jose Fonte during training. After his time with Southampton, he was loaned to Juventus, Inter Milan, and Boca Juniors.

Dani Osvaldo had multiple transfers in his record, with a £13.6 million contract in 2013 on his transfer from Roma to Southampton.

Final Thoughts

Player transfers are what make the world of football a dynamic and ever-changing sport. Players aren’t stuck in a team forever, and all the different and new additions to a team every transfer window makes every match feel new and fresh. You would never know what was coming. The best we can do as spectators and enthusiasts of the sport is enjoy the games and hope that for every football transfer update, the managers have the wisdom and experience to choose who they want to enter their teams next.

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Football Auditor

Hey i'm Emmanuel, in love with football, what's more fun than discussing football will you guys.

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