5 times Tottenham Hotspur missed out on transfer targets

#2: Joao Moutinho

Joao Moutinho could've signed for Spurs had it not been for Premier League regulations

Portuguese midfielder Joao Moutinho will be starring in the Premier League in 2018/19 for Wolves, after the Midlands club were able to secure his services for a cut-price £5m earlier this summer. Frustratingly for Tottenham fans though, Moutinho could’ve been a Premier League star way back in the summer of 2012 had the Lilywhites’ move for him not fallen through at the last minute on that summer’s deadline day.

On this occasion, Tottenham’s move fell foul of Premier League regulations regarding third party ownership of players. Moutinho’s club Porto were willing to sell, and were happy to accept Tottenham’s £24m bid for the player – who seemed happy with the move, as it offered him a chance to hook up with his former boss Andre Villas-Boas. But despite Moutinho stating that he was “minutes away” from being a Spurs player, the move fell through and he ended up spending another season at Porto before moving to Monaco.

The devil turned out to be in the details – of the £24m that Tottenham were offering, 25% of the profit was to go to Sporting Lisbon, who had sold Moutinho to Porto in 2010. That wasn’t a problem – but the fact that 15% was also to go to a “third party investor” who had bought a percentage of the player’s rights in 2011 ended up being a major stumbling block, with Premier League rules preventing any third party ownership in players.

Tottenham simply couldn’t sort the issue out in time, and so they ended up missing out on a player who could’ve become a key figure for Villas-Boas in 2012/13.