Meanwhile, Tottenham are said to have had a bid rejected for West Brom forward Saido Berahino by BBC Sport among others, with no news of progress when it comes to Crystal Palace winger Yannick Bolasie either.
All the while, the north London side's existing wingers have toiled. Erik Lamela is bitterly disappointing fans right now - and has even been linked with a Tottenham exit by the Independent. Nacer Chadli's consistency has been questioned and Christian Eriksen appears to have too much of a burden being placed on his creativity.
Alex Pritchard hasn't broken into Mauricio Pochettino's side yet and Andros Townsend... well, he's Andros Townsend.
Which brings us back to Cuadrado. Since joining Chelsea for a fee reported by the Daily Mail to be £27 million, the 27-year-old has flattered to deceive. But he's barely been given a chance - and disappointing at a side that is challenging for the Premier League title doesn't really give much of an indication as to how a player could do slightly lower down the table.
Should Spurs try and make a move?
Daniel Levy has left his summer transfer business until the 11th hour once again but, now that Cuadrado is reportedly available for loan, that may work to Tottenham's benefit. The Colombian is a World Cup star and a forward who tore Serie A to shreds.
Admittedly, the fact Lamela came from Serie A confirms an element of risk factor. But Spurs were said to be after both Mohamed Salah and Victor Moses from Chelsea. Why not now try Cuadrado?
After all, Kevin De Bruyne didn't succeed under Jose Mourinho - but look at him now. There may yet be a player left in the Chelsea winger - and one that could solve a very big problem for Tottenham.