Manchester United have failed in a bid to take Real Madrid left-back Fabio Coentrao on a season-long loan - compounding the pain of missing out on Leighton Baines and Athletic Bilbao's Ander Herrera.

United boss David Moyes had hoped to pull off a major coup by capturing Portugal international Coentrao at the 11th hour, but the paperwork was apparently not completed in time and the player will remain at the Spanish giants.

The news will be greeted with dismay by United fans, who have been less than impressed with the club's dealings during the window.

And it leaves Moyes in the tricky position of needing to explain to Patrice Evra why he felt another left-back was required.

One theory was that Coentrao would have operated at left-back, with Evra in a more advanced role, which he played during his early years as a professional.

Nevertheless, Evra's form last season and the early weeks of the current one was not that of a man who needed replacing.

Now the France star will remain in his favoured role, with Alex Buttner also set to stay at Old Trafford as his deputy following talks over loan deals with both Besiktas and Celtic.

Coentrao has yet to make a La Liga appearance for Real this season and was keen to move following the summer departure of former Madrid boss Jose Mourinho, who brought his compatriot to the Bernabeu in 2011.

The 25-year-old.