According to reports from Plaza Deportiva, via Football Espana, Tottenham's €22m (£20m) bid for Valencia right-back Joao Cancelo has been rejected.
Tottenham are looking for a new right back after Kyle Walker's record £50m move to Manchester City earlier this summer.
After the departure of Walker and with Kieran Trippier sidelined with injury, Mauricio Pochettino was forced to play 20-year-old Kyle Walker-Peters at right-back against Newcastle on Sunday.
Although Walker-Peters did exceptionally well, picking up the Man of the Match award for the game, Pochettino is still thought to want a more senior right-back to boost his squad depth.
Tottenham are yet to sign a player this window, with fans becoming increasingly frustrated as Spurs sell without buying.
In contrast most would have thought that Pochettino would be building up his squad depth as Tottenham look to challenge in both the Premier League and Champions League.
Nevertheless, Tottenham now look to be trying to make their first signing, but only have a few weeks remaining to sign another right-back.
Pochettino’s side will also need to up their bid for Cancelo, as they have to match Valencia’s reported €25m (£22.7m) price tag if they want to get their man.
Signed from Benfica in 2015 for €15m, the 23-year-old has made 73 La Liga appearances for Los Che, making him a regular in the Valencia side.
Out of all the defenders in La Liga, only Filipe Luis (145) has completed more dribbles than Cancelo (114) in the last two seasons. This makes Cancelo a perfect fit for Tottenham's wing-back style of play, as they rely on their wide defenders for much of their pace and creativity from wide areas.
Tottenham had been eyeing up moves for Benjamin Henrichs of Bayer Leverkusen and Jeremy Toljan of Hoffenheim, however they now look set to sign Cancelo with an increased bid expected in the coming days.