Fabio Coentrao missed out on a deadline day move to Manchester United after the Red Devils ran out of time to complete the deal.
New United boss David Moyes was keen to take the Portuguese international on a season long loan to provide competition to Patrice Evra for the left-back spot.
But with all their efforts focused on closing the deal for Marouane Fellaini, the Old Trafford outfit were left short of time.
Coentrao had been keen on a move away from the Santiago Bernabeu all summer after losing his place in the team to Marcelo.
The 25-year-old, who joined the club from Benfica in 2011, was linked with his previous team in Portugal as well as Premier League side Chelsea, now managed my Jose Mourinho.