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11 worst Premier League transfers of all time as four Man Utd flops included There have been some HOWLERS in the transfer market - but who is the worst? 11 of the worst Premier League transfers of all time Express Sport counts down 11 of the worst Premier League transfers We all secretly love the hustle and bustle of the transfer window. From the weeks of endless speculation and that dopamine hit when your club spends big on a new arrival: there really isn't much like the summer transfer window. But when the excitement of new signings wear off, sometimes fans are met with the reality that the player thier club has splashed millions on isn't actually very good. Every club has a stinker, but some have more than others! So to celebrate the final week of the transfer window getting underway, we've picked out some of the worst transfers in Premier League history. It should cause some debate, so get involved in the conversation and let us know who you think is the worst transfer of all time. 11 - Kalvin Phillips to Man City (£45m) A transfer that made sense at the time, but quickly left you scratching your head. Kalvin Phillips swapped Leeds United for Manchester City in the summer of 2022, but barely saw any game time during his first 18 months at the club. By January 2024 the seemingly never-ending loan moves started, with West Ham United up first, before Ipswich Town followed the next season. He eventually wound up at Sheffield United, which is where the Yorkshireman will spend the upcoming campaign. 10 - Angel Di Maria (£60m) Angel Di Maria was the big marquee signing in the summer of 2014, but fast forward 12 months and he was already gone. The Red Devils splashed out a whopping £60m on his services, but it quickly became clear the Argentine wasn't compatible with the Premier League. The only reason this transfer isn't in the top five is that United did manage to recoup £44.3m when selling Di Maria to Paris Saint-Germain the following summer. 9 - Romelu Lukaku to Chelsea (£97.5m) On the back of winning the Champions League, Chelsea adding Romelu Lukaku to their attack felt like the missing piece. Instead, what followed was somewhat of a disaster, with Lukaku managing a season of just 15 goals in 2021/22. Just one season into his return to Chelsea, the striker was loaned to Inter Milan, then Roma and eventually Napoli, where he joined permanently in 2024. 9 - Andy Carroll to Liverpool (£35m) January 2011 was a tale of two transfers for Liverpool. In one corner, Luis Suarez, in the other... Andy Carroll. The irony being, it was the £35m Carroll that was the more expensive of the two. Suffice to say it didn't work out for the Englishman at Anfield, with Carroll nowadays kicking around at Daggenham & Redbridge in non-League.