The transfer window can inspire a range of surprising storylines over the course of a summer but at its best, the drama of dealmaking can pave the way for a frantic race to the finish line and a unique genre of soccer chaos – deadline day shenanigans.
Bizarre stories are not a guarantee every deadline day but when they present themselves, they are hard to forget. Many of them are underlined by someone‘s desperation to get a deal done, be it a club or a player, but the mishaps are wide-ranging. Clerical errors are an unfortunate part of the experience, while some players have taken matters into their own hands to get what they want.
The most memorable deadline day stories, though, are the ones of failure. While it is not uncommon for teams to miss out on their transfer targets, it is exceedingly rare for a deal to actually collapse at the last minute. The innumerate number of deals that happen every year, though, means there is always the possibility that things go haywire, leaving players and teams at an impasse once the window is shut and normal activity is supposed to resume.
Here’s a look back at some of the wackiest deadline day moments.
Joao Palhinha‘s failed move to Bayern Munich
Bayern Munich were going through the processes of completing a deadline day move for Fulham midfielder Joao Palhinha, who was photographed entering the German club’s training ground in September 2023. He reportedly completed his medical and posed for photos in a Bayern jersey but by day’s end, he was back on his way to London, the deal collapsing at the last minute. Bayern were unable to strike an agreement with Fulham for Palhinha’s transfer, the English club failing to line up a replacement before the transfer window closed in Germany. Another year in London was in store for Palhinha, who ended up playing 39 games for Fulham in the 2023-24 season before getting his long-awaited move to Bayern the following year.
Things have not panned out for him so far in Munich, though — he only played 17 Bundesliga games that season and made just five appearances in the UEFA Champions League, joining Tottenham Hotspur on loan this season with the hopes of earning more playing time.
Real Madrid, Manchester United and a fax machine
Real Madrid made a push to sign then-Manchester United goalkeeper David de Gea in 2015 and send Keylor Navas the other way, but the swap deal was unable to go through before the deadline, inspiring a war of words between the two clubs. Los Blancos issued a statement claiming that Navas requested small changes to the agreement that slowed down the whole process but that both players had signed off by the deadline, accusing United of holding up the deal so that it could not be completed by issuing a 10 point statement. The Red Devils denied wrongdoing, saying they submitted the necessary paperwork two minutes before the deadline but were “delighted” that de Gea was sticking around.
The unsubstantiated rumor is that United’s fax machine got in the way but de Gea has promised to share the details once his career is over. “I will speak about all of that when my career is over,” he told Cronache Di Spogliatoio earlier this year. “When things don’t happen, it’s for a reason. It was close but the transfer wasn’t completed.”
Blackburn Rovers press the wrong button
Sometimes there are accusations of foul play and other times, a clerical error is all it takes for a deal to collapse. Take, for example, Duncan McGuire‘s proposed move to Blackburn in February 2024, which fell through not once but twice. McGuire was reportedly catching a connecting flight at New York’s John F. Kennedy International Airport, en route to Manchester from Orlando City’s preseason camp in Mexico, when Rovers pulled out of the deal due to a lack of funds. The transfer was finally back on track on deadline day and the club thought it was actually done by the time the window closed. As it turned out, though, a staff member pressed “save” instead of “submit paperwork” and Rovers later lost an appeal to see the deal through. McGuire has been with Orlando ever since.
Ryan Babel leaves Liverpool via helicopter
Ryan Babel was spotted leaving Liverpool in a helicopter in August 2010, with many speculating that he was leaving the Reds on a deadline day deal. He confirmed as much in a Talksport interview 13 years later, admitting that Liverpool woke him up on an off day with the hopes of completing a swap deal for Carlton Cole and that West Ham arranged for a helicopter to bring him to London. He described that helicopter ride as “one of the worst experiences” because of constant turbulence and that upon arrival in London, the deal fell through because West Ham wanted him to sign a five year contract when he was told it would be a loan deal. There was no helicopter on the way back.
“Funny enough, instead of flying us back in a helicopter, they dropped me off at a train station like ‘yeah, go back to Liverpool,'” he said. “So, that was quite an experience.”
Peter Odemwingie shows up unannounced
There is one deadline day story that stands above the rest — Peter Odemwingie’s failed move from West Bromwich Albion to Queens Park Rangers. The clubs agreed a fee but a deal never actually materialized, though Odemwingie was not going to take no for an answer. Days after taking to social media, upset that West Brom had rejected a transfer request, Odemwingie drove down to Loftus Road, QPR’s stadium, and parked outside the venue hoping the deal would go through. He did interviews from the front seat of his car but he was never actually let into the building, and so he returned to West Brom to finish the season mostly as a benchwarmer and attack the club a few more times on social media. He finally got his wish with a summertime move to Cardiff City and pivoted to golf after retiring from soccer in 2019.
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