Spurs are currently in the midst of a poor run of form, and Mauricio Pochettino is arguably experiencing his first mini-crisis since taking over as manager of the club in May 2014.
One issue that is surely not helping Tottenham at the moment is Danny Rose's outspoken nature, and his insistence on making it clear that he is unhappy with playing a peripheral role at the club.
Whilst it remains unclear whether he will remain at Spurs beyond this season, the way things have been going, it would take a brave man to bet against him heading for the exit door either in January or the summer.
If the 27-year-old does eventually leave, Pochettino will obviously have to sign a replacement, and an interesting option for them could be Reds ace Andrew Robertson, after Italian media outlet Corriere dello Sport reported that Jürgen Klopp has been underwhelmed with the 23-year-old since his summer switch from Hull City.
They claim that Liverpool are interested in Roma left-back Emerson Palmieri - a signing that would surely see Robertson fall even further down the pecking order at Anfield.
And the Lilywhites should test the Merseyside outfit's resolve by making an offer for the Scotland international.
Despite making just two Premier League appearances for Liverpool this term, Robertson still has a lot to offer, and his playing style is perfectly suited to Tottenham's system.
He is wonderfully gifted on the ball, can operate as an orthodox full-back, or in a more advanced wing-back role, and he possesses an impressive engine.
Whether Klopp would entertain the idea of selling Robertson so soon after bringing him to the club is debatable, but if the German does in fact bring Palmieri to Anfield, Tottenham would surely have a good chance of convincing the Reds to sanction the Scot's exit.
And if Pochettino manages to bring the Liverpool man to Spurs, it could turn out to be a signing of real significance for the club.