Andre Villas-Boas was keen on bringing the Portuguese left-back to north London as part of the deal which saw Gareth Bale move to the Spanish capital, but an agreement could not be found.
The former Benfica star has failed to earn himself a regular place in Carlo Ancelotti's starting XI and could be available - possibly on loan - when the window reopens.
The left-back had been associated with a move to Old Trafford over the summer but a deal couldn't be thrashed out before the deadline, a scenario talkSPORT said "reduced the player to tears."
Although it may not be Coentrao's original choice, a deal that was reportedly proposed as part of Gareth Bale's £85 million transfer to the Bernabeu—per Jack Wilson of the Daily Star—may eventually come to pass this winter.
So far this season, Coentrao has made just four starts under Carlo Ancelotti, playing the full 90 minutes on two of those occasions. That's after the defender featured in only 16 La Liga games under compatriot Jose Mourinho last term.
But it's another Portuguese manager, Villas-Boas, who is supposedly now looking to give Coentrao another chance at top-flight football—this time in Tottenham white.
Primarily a full-back, the 25-year-old is also an asset in midfield or as a winger, cover that Villas-Boas could do with considering his team are still coping with the loss of Bale.
Having said that, his more immediate need would be in defence right now, given that Spurs' summer midfield recruitment drive has given them a wealth of options in that area.
Coentrao's more immediate concern is his left ankle, which buckled during Madrid's weekend clash with Rayo Vallecano.
Drayton's report also claims that a short-term deal could be an option for the North London outfit, which would suit Coentrao as a player looking for game time in a World Cup year.
Danny Rose is currently struggling with injury so Spurs need cover for Jan Vertonghen at left-back.
Tottenham allowed Benoit Assou-Ekotto to join QPR on loan over the summer, while Kyle Naughton is capable of playing on the left side of defence, but he is too inexperienced for where Villas-Boas wants to take his side.