The transfer window is only open twice a year, giving clubs precious opportunities to strengthen their squads. Transfer deadline day, in particular, is notoriously hectic—often nothing is certain until well after midnight.
Here are 15 transfers that everyone expected to happen, but due to human or technical errors, collapsed at the final hurdle.
Fabio Coentrão (Real Madrid → Manchester United, 2013)
What happened: Manchester United scrambled to sign a left-back after missing out on other targets and reached a loan agreement with Real Madrid for Coentrão. However, the necessary paperwork was submitted too late on deadline day, and FIFA refused to approve the transfer.
Peter Odemwingie (West Bromwich Albion → QPR, 2013)
What happened: In one of the most bizarre deadline-day incidents, Odemwingie drove to QPR’s training ground to force a move. However, West Brom never finalized terms with QPR, leaving Odemwingie awkwardly stranded outside Loftus Road and forced to return to his old club.
Bryan Ruiz (Fulham → Levante, 2015)
What happened: Fulham and Levante reached a last-minute agreement for a loan deal, but the Spanish side’s paperwork reportedly arrived just after midnight. La Liga refused to ratify the transfer, so Ruiz remained at Fulham against expectations.
David De Gea (Manchester United → Real Madrid, 2015)
What happened: Perhaps the most famous “fax machine” saga in football history. Manchester United and Real Madrid reportedly agreed on a swap deal involving De Gea and Keylor Navas, but crucial documents arrived after the Spanish deadline, keeping De Gea at Old Trafford.
Alexis Sánchez (Arsenal → Manchester City, 2017)
What happened: Sánchez was eager to reunite with Pep Guardiola, and Arsenal had initially agreed to sell him. But the Gunners’ attempt to sign Thomas Lemar as a replacement fell through. Without Lemar, Arsenal pulled the plug on Sánchez’s deal just before the window closed.
Adrien Silva (Sporting CP → Leicester City, 2017)
What happened: After selling Danny Drinkwater to Chelsea, Leicester rushed to sign Sporting CP midfielder Adrien Silva. However, the club submitted paperwork an alleged 14 seconds late. FIFA rejected the registration, leaving Silva in limbo until the next transfer window.
Emmanuel Adebayor (Tottenham Hotspur → West Ham United, 2015)
What happened: Adebayor looked set to join West Ham on deadline day, with Tottenham eager to offload him. However, Spurs chairman Daniel Levy reportedly backed out due to disagreements over wages, effectively ending the transfer at the last moment.
Thomas Lemar (AS Monaco → Arsenal, 2017)
What happened: Arsenal were ready to break their transfer record to sign Lemar, reportedly bidding over £90 million. Despite advanced talks, time ran out before the final paperwork and personal terms could be nailed down, and Lemar stayed at Monaco.
Demba Ba (Chelsea → Arsenal, 2013)
What happened: Real Madrid tabled multiple massive bids (reportedly up to €200 million) for Mbappé in the final days of the summer window. PSG refused to accept any offer, determined to keep their star. When the deadline passed, Mbappé remained in Paris.
Paulo Dybala (Juventus → Tottenham Hotspur / Manchester United, 2019)
What happened: Both Spurs and Manchester United tried to land Dybala in the closing days of the summer window. Though Juventus agreed on fees, Dybala’s image rights and agent fees caused complications. Negotiations dragged on until it was too late, and he stayed in Turin.
João Moutinho (FC Porto → Tottenham Hotspur, 2012)
What happened: Spurs manager André Villas-Boas pushed for Moutinho’s signing, and the clubs reached a tentative deal late on deadline day. But third-party ownership issues and personal terms took too long to resolve, causing them to miss the deadline by mere minutes.
Nabil Fekir (Lyon → Liverpool, 2018)
What happened: Fekir underwent a medical and even posed for unofficial promotional materials. However, Liverpool reportedly had concerns about an old knee injury, and negotiations stalled right before signing. Ultimately, the deal collapsed at the last second.
Loïc Rémy (QPR → Liverpool, 2014)
What happened: After triggering a release clause, Liverpool brought Rémy to their U.S. pre-season tour for a medical. Something in the medical results allegedly unsettled Liverpool, and they withdrew the offer just before finalizing. Rémy later joined Chelsea instead.
Robinho (Real Madrid → Chelsea, 2008)
What happened: Chelsea were so confident of signing Robinho, they printed shirts bearing his name. Yet on deadline day, newly cash-rich Manchester City swooped in with a higher bid. Real Madrid accepted City’s offer, and Robinho’s move to Chelsea was scuppered at the last moment.
