For the duration of the transfer window and also for the most part of last season, Manchester United had been linked to or interested in English international Leighton Baines but at the window drew to a close, they still hadn't got their man.
But instead in the last few hours they made an attempt for Coentrao who had not been very happy with the treatment at Real Madrid since arriving there from Benfica a couple of seasons ago.
But for Coentrao to leave, Real Madrid had to sign a replacement in the form of Granada left-back Guilherme Siqueira with the league giving the green light to the signing but Siqueira had already made a loan move to Benfica, halting the proposed deal.
Manchester United were however able to negotiate a deal for Baines's teammate Marouane Felliani on the final day to relieve a bit of pressure on the club to sign a top quality player.