A move from the Santiago Bernabeu to Old Trafford was looking highly likely for Fabio Coentrao until the injury of David Alaba in Bayern Munich's Champions League game with Roma on Wednesday.
With Real Madrid sniffing around the Austrian full-back, the arrival of Alaba to the Spanish giants would leave the door open for Coentrao to leave the club.
With United showing clear signs of interest in the Portuguese man as they are looking to bolster their defensive options in the winter transfer window, a move on for the 26-year-old looked fairly straightforward.
However, with the unavailability of Alaba for Madrid due to a three month knee ligament injury, then the La Liga club will be in need of Coentrao's services which therefore means he may have to put a move to the Red Devils on hold until the summer.
Madrid gaffer Carlo Ancelotti had confirmed after Alaba's injury that the club would only allow Coentrao to leave on the condition that the Austrian completed a move from Bayern Munich.
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Alaba's quality was explained by Pep Guardiola after Bayern's 2-0 home victory against Roma on Wednesday as he announced that "a great player has been lost who plays fantastic football".
Louis van Gaal will be expected to be on the instant look out for another target to bring in so that United's defensive options can be improved significantly before it is too late. After all, he currently holds a worse record than David Moyes.