Liverpool have been left red-faced on a number of occasions in the transfer market

Liverpool will be hoping to strengthen new manager Andoni Iraola's squad this summer. But the Reds have found themselves red-faced on more than a few occasions during previous transfer pursuits.

With Arne Slot replaced by former Bournemouth boss Iraola at the helm, Liverpool's fifth-place Premier League finish last season is something the club will be desperate to forget about. To achieve that, they will undoubtedly need to overhaul their squad and have already taken steps to do so.

Victor Munoz has been brought in from Osasuna for £34.5million, while a trio of first-team veterans - Mohamed Salah, Andy Robertson and Ibrahima Konate - have all left upon the expiry of their contracts. Jeremy Jacquet has also arrived after his £60m switch was agreed back in January.

However, further reinforcements are needed and finding a replacement for Salah is an absolute priority. As the Reds chase a number of transfer targets, they'll be keen to avoid the all-too-familiar heartbreak of a deal collapsing at the eleventh hour.

Marc Guehi

Liverpool's most recent transfer nightmare involves Marc Guehi. In the closing weeks of the 2025 summer transfer window, the then-Crystal Palace captain made it abundantly clear he wanted out of the club, with just one year left to run on his contract.

This led the Reds to pursue the defender, whom they saw as a long-term successor to the ageing Virgil van Dijk. With Palace prepared to sell, they settled on a reduced £35m fee.

Guehi completed his Liverpool medical, but the transfer encountered an unforeseen obstacle. Then-Palace manager Oliver Glasner was infuriated by the sale and when a corresponding move for Brighton's Igor Julio collapsed, the deal was abandoned.

Guehi joined Manchester City in January.

Moises Caicedo

In August 2023, following the exits of Jordan Henderson and Fabinho, Liverpool desperately needed a new midfield leader and identified Moises Caicedo, who had excelled for Brighton.

The Reds submitted a British record £111m bid, which was accepted. Jurgen Klopp even announced that the deal had been completed in a press conference, but the sole complication was that Caicedo had promised Chelsea months earlier that he would join them.

He declined to travel to Liverpool for a medical. The player would subsequently sign for the west London club for £115m and Liverpool switched their attention to Wataru Endo.

Nabil Fekir

Five years before the Caicedo saga, Nabil Fekir appeared destined to become a Liverpool player. The then-Lyon captain had rapidly established himself as one of Ligue 1's brightest talents and was World Cup-bound with France.

The midfielder travelled to Liverpool, completed his medical and even had a shirt number selected. The contract was signed and the official media was finished, but at the final moment, the deal fell through.

Initially, reports suggested concerns over a knee problem had been raised, but Fekir later blamed his agent for the deal not going through. It should be noted that the precise reason behind the transfer's collapse remains unclear.

Fekir, who was heavily linked with a switch to Manchester United following this breakdown, subsequently joined Real Betis. The World Cup winner last featured for UAE Pro League outfit Al Jazira and is currently without a club.

Dani Alves

Dani 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.

Following their 2005 Champions League triumph, former Reds boss Rafa Benitez pinpointed Sevilla's Alves as a full-back capable of transforming his side's right side. With personal terms agreed, he urged the board to sanction the deal.

Sevilla wanted £8m for Alves, but the Liverpool hierarchy refused to stump up the cash. Instead, they splashed £6.7m on Jermaine Pennant and Alves remained at Sevilla for two further seasons, claiming back-to-back UEFA Cup victories.

He joined Barcelona in 2008 and went on to represent Juventus and PSG, finishing his career with an extraordinary 43 trophies.