Liverpool saw transfers for record signing and World Cup winner fall through

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Liverpool are expected to be busy this summer but not all of their past transfer approaches have gone to planLiverpool will hope they can bolster new manager Andoni Iraola's squad this summer. But the Reds have been left with egg on their face during plenty of past transfer pursuits.With Arne Slot supplanted and former Bournemouth boss Iraola at the wheel, Liverpool's fifth-place Premier League finish in the season just gone is something the club will look to put behind them.

In the final weeks of the 2025 summer transfer window, then-Crystal Palace skipper Guehi made his intention to leave the club clear with one year remaining on his deal.This prompted the Reds to approach the defender, whom they viewed as a long-term replacement for the ageing Virgil van Dijk. With Palace wanting to cash in, they agreed to a cut-price £35m deal.Guehi passed his Liverpool medical, but the transfer hit an unexpected snag.

Jurgen Klopp even confirmed that the deal had been done in a press conference, but the only issue was that Caicedo had given Chelsea his word months prior that he would sign for them.He refused to travel for a medical at Liverpool. The World Cup winner last played for UAE Pro League side Al Jazira and is currently a free agent.Dani AlvesDani Alves made over 400 appearances for Barcelona, but the right-back could have ended up at Liverpool in 2006 were it not for the club's penny-pinching.On the back of their 2005 Champions League win, former Reds boss Rafa Benitez identified Sevilla's Alves as a full-back who could transform his team's right flank.