2. Not Signing Fabio Coentrao
Spurs were in an ideal position to get a good player as part of the Gareth Bale deal when Real Madrid came knocking, so to have come away with 'only' money from it is actually quite disappointing (obviously it was a huge amount of money, but still...). Fabio Coentrao, in my humble opinion, would have been the missing piece in the Spurs jigsaw. He would, quite simply, have completed the team, ensuring every position on the pitch was filled with a player capable of challenging at the top. Of course, it may have been the case that Coentrao flat-out refused to speak to Spurs, in which case replace his name in this entry with another left back. Spurs were linked with Federico Balzaretti, Alberto de la Bella and Alvaro Pereira - all of whom would have been an upgrade on the current left backs - but they failed to even bring in any of them on loan.