#4 Toby Alderweireld to Manchester United
Mourinho and Manchester United were in search of a defender over the summer and their search had ended on Toby Alderweireld of Spurs, fresh from a solid World Club with Belgium. Multiple news sources reported that Alderweireld was on the verge of joining United in a £60million move. There were reports that the player was desperate to join United, even willing to run down his contract if required. But with each passing day, there seemed to be no signs from either United or Tottenham that the move was about to happen.
It then reported that Tottenham was waiting for a player plus cash deal for Alderweireld and the London club were waiting for a bid from United on Deadline day. The main difference between both clubs, it was said, was with the valuation of the centre back. Tottenham wanted £75million for Alderweireld, whereas United refused to pay that much. The Transfer Deadline Day arrived in England and passed away without much fuss and Alderweireld stayed where he was.
It was later revealed that the United Board did not trust Mourinho with the money to buy the centre-back, as he already had Bailly and Lindelof in the squad. On Monday night, as Tottenham made light work of United, Mourinho could be forgiven for knocking on Ed Woodward's door and telling him - "I told you so!".