Time is running out for Tottenham.
In four years since manager Mauricio Pochettino’s arrival, Spurs have been transformed into a perennial top-four side and genuine title contenders.
They’ve held onto their best players, too, time and again resisting the advances from the world’s biggest clubs for their biggest talents.
And, with a new stadium just over the horizon, the club are in their best standing since the advent of the Premier League more than a quarter of a century ago.
But the trophy cabinet remains strikingly bare, many of their stars are ageing and, with their UEFA Champions League campaign already in the balance, should this season end in disappointment once more, the rebirth could be set to flatline.
“We believe that we can beat them,” said Pochettino this week. “But when you watch [our Champions League draw] PSV again, you need to force the game more to the opponent and force mistakes and need to score more before.”
Attempting to press City into mistakes has proved a dangerous ploy, but so too has sitting off them. Their last two outings versus Pep Guardiola’s side brought two defeats and a 7-2 aggregate deficit as their press was first bypassed and then noticeable only in its absence.
Spurs have now lost 10 of their last 15 Premier League games against Man City (W4 D1), having lost just three of their first 27 games against them in the competition. Times have most certainly changed.
Tottenham’s Premier League hopes will not be mathematically determined by Monday night’s clash on a Wembley pitch ravaged by the NFL this past weekend, but the nature of their evening may yet define their future – both short and long term.
Since Pochettino became Spurs manager in 2014-15, only Arsenal (37) have won fewer points in Premier League games between the ‘big six’ than the Lilywhites (54). Victory over City, then, could provide a vital mental boost as they appear set for an early European exit that would provide an opportunity to concentrate fully on that elusive Premier League title.
“It's a different season,” insists Pochettino. “I promise you we are working more than the previous season. We are thinking more, we spend more time analysing the team.”
There was plenty of analysis to do following their disappointment in Eindhoven, but Tottenham have lost just two of their last 21 Premier League games at Wembley Stadium (W15 D4 L2) and three points will see them leapfrog City into joint-second.
And Monday nights have proved fertile hunting ground. Tottenham have won seven and lost none of their last nine Premier League games played on Monday (D2), with their last defeat coming against Norwich in April 2012 (1-2).
It’s now or never. Tottenham’s time has to come now or, before they know it, it may well be gone.
The stakes are high. The pressure is on.