5 Clubs With The Worst Transfers in Football History

In football, a big signing brings big expectations, but sometimes things just don’t work out.

Some transfer mistakes are bigger than others, though. So, we decided to rank the worst transfer moves of all time. First up, the criteria on which we based our ranking: for us, expectations upon signing, transfer fee, sell-on fee, longevity at the club they signed for, and statistical performance all come into the equation.

FC Barcelona – Philippe Coutinho and Antoine Griezmann

With those factors in mind, we ranked Philippe Coutinho’s move from Liverpool to Barcelona for approximately 121.5 million back in 2018 as the worst deal of them all. Whilst Liverpool used that money to help build a Premier League-winning side, Barcelona sold Coutinho for a loss of around 100 million in 2022, and the Brazilian now finds himself playing in Qatar, on loan from Aston Villa. He managed just 25 goals and 14 assists in over 100 games for Barcelona.

The Catalans made a mess of things when it comes to the second on our list, too. They activated Antoine Griezmann’s 108 million release clause at Atletico Madrid in 2019, only for Griezmann to return to Atletico 2 years later, first on loan and then on a permanent deal, for half the price he left for.

Real Madrid – Eden Hazard and Jonathan Woodgate

We’ll leave Barcelona alone for the rest of this list, but their fierce rivals Real Madrid have also made some high-profile mistakes. Eden Hazard’s 103 million (rising to 135 million) move from Chelsea in 2019 comes in third. To be fair, injuries were a key factor in this deal not working out, with Hazard playing just 76 times in Madrid before retiring from football in 2023 at the age of just 32.

Injuries also played a part in Real’s second entry on this list: the signing of Jonathan Woodgate from Newcastle United in 2004 for 6 million. Woodgate spent a year on the sidelines injured, and then when he finally made his debut, he was sent off and scored an own goal. He was labeled the worst signing in the 21st century by Madrid newspaper Marca, but luckily for him, he’s just seventh on our list.

Chelsea FC – Lukaku, Shevchenko, Torres

Chelsea’s consistent inability to sign top-level strikers accounts for no less than three entries in the top 10. In fourth place, we have Romelu Lukaku’s 97.5 million pound return to the club in 2021. Sixth is Andriy Shevchenko’s 39.5 million move in 2006, and in 10th, we have Fernando Torres’s 50 million pound move from Liverpool in 2011. Between them, they played over 300 games for Chelsea but combined for just 82 goals.

Manchester United – Angel Di Maria and Alexis Sanchez

Manchester United also have an expensive mistake in them: Angel Di Maria’s 60 million pound move from Real Madrid in 2014 never worked out and is eighth on our list. But above him, we have Alexis Sanchez, who despite not costing a fee (he was swapped for Henrikh Mkhitaryan) is fifth on the list because his staggering £560,000 a week wages were such a financial albatross for the club for such a long time.

Liverpool FC – Andy Carroll and Mario Balotelli

Finally, Liverpool can feel smug for selling some of the players on this list, but the signings of Andy Carroll for £35 million (worth of the Torres money) eighth on our list and the £6 million disastrous move for Mario Balotelli, 11th on our list, are two transfers they surely wish they never made.