5 times clubs missed out on Deadline Day signings

#3 Joao Moutinho to Tottenham Hotspur, 2012

Joao Moutinho's move to Spurs fell apart due to the issue of third-party ownership

After selling midfield star Luka Modric to Real Madrid for £30m in the summer of 2012, then-Tottenham boss Andre Villas-Boas looked all set to turn to one of his countrymen as the Croatian’s replacement. Moutinho – at the time playing at home with Porto – had starred in Portugal’s Euro 2012 campaign that saw them make the semi-finals, and seemed like he’d fit right into AVB’s plans at White Hart Lane.

A £24m bid was tabled by Spurs; Porto accepted the offer, and Moutinho made his way to London for contract discussions. But with the deal seemingly on the table, at the very last minute – Moutinho himself has stated he was literally “minutes away” from being a Tottenham player – it suddenly fell through and the Portuguese midfielder was left at Porto for another year before moving to Monaco.

Paperwork – or a lack thereof – was initially blamed for the deal going awry, but it turned out to be more than that. Of the £24m Spurs were offering, 25% of the profit on the player was to go to Sporting Lisbon, who had sold him to Porto, but 15% was also due to a “third party investor”, who had bought that percentage of the rights to the player from Porto in 2011.

With the Premier League’s rules barring any third-party interest in players, Spurs simply couldn’t get the deal done quickly enough. It was an awkward situation and in the end, Tottenham came away empty-handed, while Moutinho remains at Monaco having signed with them the following summer.