As the final week of the transfer window gets underway, Express Sport has ranked the 11 worst Premier League transfers of all time. The list includes four Manchester United signings, with a mix of record fees and high-profile loan moves that failed to deliver.
Phillips and Di Maria among the worst
Kalvin Phillips is ranked 11th after his £45m move from Leeds United to Manchester City in the summer of 2022. He barely saw game time in his first 18 months at the club, and by January 2024 a series of loan moves began, first to West Ham United, then Ipswich Town, and eventually Sheffield United, where he will spend the upcoming campaign.
Angel Di Maria is 10th. Manchester United paid £60m for the Argentine in the summer of 2014, but he was gone within 12 months. United managed to recoup £44.3m when selling him to Paris Saint-Germain, which is why the transfer is not ranked higher.
Lukaku and Carroll fail to deliver
Romelu Lukaku is joint 9th. Chelsea signed him for £97.5m after winning the Champions League, but he managed just 15 goals in the 2021/22 season. He was loaned to Inter Milan, then Roma, and eventually joined Napoli permanently in 2024.
Andy Carroll is also joint 9th. In January 2011, Liverpool signed both Luis Suarez and Carroll, with Carroll costing £35m – more than Suarez. The move did not work out for the Englishman at Anfield, and he now plays for Dagenham & Redbridge in non-League.
The full list continues with more signings, and Express Sport invites fans to debate who they think is the worst transfer of all time.
