He has endured a stop-start campaign with the Lilywhites, and has hardly endeared himself to the Spurs faithful, after making disparaging comments regarding the club's ambition.
It is not only Spurs who now face a fight to hold onto their prized asset.
Tottenham chairman Daniel Levy has made a claim about the futures of two of his star players amid links to Real Madrid. "He loves Tottenham and everyone wants to win - us, the club, (chairman) Daniel Levy, the players, the fans - and wants to win in the place you love".
The statement from Levy will therefore cool the situation and deal a killer blow to Zinedine Zidane's hopes of doing any deal for the player.
Philippe Coutinho's €160m transfer from Liverpool to Barcelona at the weekend will have only served to reinforce the view that, if Tottenham were ever to consider selling Kane, the England forward would command a fee closer to that paid for Neymar than Coutinho.
The player finished above Cristiano Ronaldo and Lionel Messi in goals scored for 2017 and Los Blancos are looking for a man to spearhead their attack.
Which is why Levy is already getting his claws out and at the ready. Real's interest in Kane has seen Levy's guard go up. "They need new motivation and challenges".
Midfield: Pochettino is set to recall Eric Dier after he was rested against Wimbledon so Victor Wanyama could drop back to the bench after starting his first game of the season last week.
Mauricio Pochettino insists Harry Kane would rather win trophies at Tottenham than anywhere else.
Their lack of activity has come in stark contrast to most of the Premier League's top six.
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