Tottenham Hotspur will attempt to lure Luke Shaw away from Southampton should they fail with a revived bid to sign Fabio Coentrao from Real Madrid.
Both Spurs and Manchester United were keen to bring the Portuguese international to the Premier League during the summer transfer window after the 25-year-old admitted he would consider a move away from the Bernabeu.
Wrangling over the full back's wages were reportedly the cause of his failure to seal a move to White Hart Lane, but Andre Villas-Boas remains keen to add the defender to his squad with the left back area of his team the one position where he is desperately lacking in depth.
But should the club fail to strike a deal for the former Benfica star when the transfer window reopens, Tottenham will then shift their focus onto 18-year-old Shaw, who is also a reported target of Chelsea and Manchester United, according to the Evening Standard.
Shaw is considered one of the most promising young defenders in the Premier League having become Southampton's number one choice on the left hand side of defence following the club's promotion back to the Premier League following the 2011/12 season.
However, Tottenham could face a strong challenge in convincing the England Under-21 star to leave St Mary's. The teenager signed a new long term deal with the club in July this year and has recently voiced his desire to remain with Mauricio Pochettino's side for the foreseeable future.
"I don't really take notice of things that are written about me - it is frustrating at times, but I just laugh it off," Shaw was quoted as saying earlier this week.
"They [the media] don't know anything because they aren't around the training ground and in the dressing room with me.
"They should know that I've signed a contract at Southampton and I'm not even thinking about moving.
"I am happy at Southampton because I'm playing football, which is exactly what I want to be doing."
"There are a lot of people out there that like to twist things - especially on social media - but I've said a lot of times that I am happy here, so I'll just carry on.
"I think people are starting to realise what sort of a club Southampton is. We are young and ambitious, and we want to go places in the next couple of years."
With both Coentrao and Shaw in his sights it would appear Villas-Boas is keen to add another left back with the currently injured Danny Rose his only natural option in that position. Jan Vertonghen and Kyle Naughton have both deputised in Rose's absence, but it is understood the Portuguese coach is eager to add a more orthodox option to the left hand side of his defence.