Liverpool’s worst transfer window of all-time included left-back ‘mistake’ and £4.5m failure

Add as preferred source on Google

Although Liverpool fans would rather win trophies than ‘win the transfer window’, there is a certain excitement about doing big business over the summer.

The Reds have often had to cede the transfer crown to other teams, regularly underwhelming a touch when it comes to buying players.

However, in 2025, Liverpool are winning both on and off the pitch. Having claimed the Premier League title in May, the Reds have followed that up with some eye-catching deals in the window.

Florian Wirtz has followed Jeremie Frimpong in swapping Bayer Leverkusen for Liverpool, while Milos Kerkez is set to join next week. The Reds will not be finished there, either.

But as supporters rejoice in their club getting things right time and again, it is worth looking back at just how far Liverpool have come in that respect.

Rewind 15 years, and you’ll come across what was quite possibly the worst transfer window in Liverpool history.

Roy Hodgson gets off to the worst possible start

Things were not going well at Liverpool in the summer of 2010. Rafael Benitez had just left after finishing 7th, while the club were still under the rocky stewardship of Tom Hicks and George Gillett.

In came Roy Hodgson for what was the biggest job of his career up to that point. And while circumstances may have made it difficult for Hodgson, he did not help himself in the transfer market.

The addition of promising midfielder Jonjo Shelvey from Charlton in May was a decent start, and Shelvey would go on to have one of the better Liverpool careers from the motley crew of 2010.

But it was July before Hodgson made a signing of his own, bringing in Milan Jovanovic on a free transfer from Standard Liege. Although Jovanovic was clearly out of his depth, he did at least manage two goals in 18 Liverpool appearances before departing in 2011.

READ MORE: All the winners and losers of Florian Wirtz’s mega move to Liverpool

Two more free transfers followed, with Joe Cole’s capture from Chelsea creating most of the headlines. Sadly, Cole was a shadow of his former self, with a sending off on debut against Arsenal setting the tone for an underwhelming two-and-a-half years.

Fabio Aurelio returned in a bizarre move, having left Anfield once his contract had expired only one month before. Aurelio made 24 further appearances before leaving in 2012.

Goalkeeper Brad Jones and young centre-back Danny Wilson were signed for a combined £4m, but made just 36 Liverpool appearances between them, while the signing of Raul Meireles from Porto was at least one shining light from in dismal summer. Even then, Meireles pushed to leave for Chelsea just one year later.

Christian Poulsen and Paul Konchesky headline terrible list

If all of that wasn’t bad enough, Hodgson saved the worst until last, as he raided former club Fulham for left-back Paul Konchesky on deadline day.

Years later, Konchesky conceded his Liverpool move had been a ‘mistake‘ and he is certainly not the only person to believe so.

Konchesky played only 18 times for the Reds after joining for £3.5m. Proving himself to be well off the pace, he moved to Nottingham Forest on loan in January 2011. Surplus to requirements under Kenny Dalglish, Konchesky then joined Championship side Leicester City the following summer.

Another failure was the addition of midfielder Christian Poulsen from Juventus. Signed for £4.5m, Poulsen was a replacement for Barcelona-bound Javier Mascherano, but played just 21 matches before leaving for French side Evian.

Clearly, not every signing is going to be a success, and transfers are a gamble at the best of times, but for four of Hodgson’s nine signings to have left after just one year with the club just about says it all. Dark times indeed.