In an interview shortly after sealing a historic treble last season, Pep Guardiola was asked what his main objective was now he had seemingly completed his ambitious bucket list.
Guardiola’s wry, almost instant, response was: “Score a goal at the Tottenham Hotspur Stadium.”
In five previous visits before this FA Cup fourth-round meeting, City had failed to hit the back of the net a single time, losing all five matches to four different Spurs managers.
It was the sort of quirk of fate that already felt as though it had gone on far longer than felt plausible. City so nearly made it six matches here, escaping with two minutes to play.
For a long time it looked as though, just to rub it in from a City perspective, the only goal in this tepid cup tie on a nippy night was to be their own goal scored after just five minutes but chalked off for an offside that was so tight it no doubt left many Spurs fans smirking with satisfaction.
With Mateo Kovacic dictating play in a superb individual performance, Micky van de Ven and Destiny Udogie were needed to make last-ditch challenges as Spurs ensured City’s possession was not allowed to amount to anything more.
The second half offered nothing but more of the same. Julian Alvarez should have scored early on but dawdled too long and allowed Van de Ven to move across and block.
Bernardo Silva and Jeremy Doku missed chances too, while the long-awaited return of James Maddison from the bench gave Spurs fans hope that they might nick a winner and condemn City to more heartache here.
Kevin De Bruyne came on too and inexplicably slammed wide of the goal with a shot that looked all the world to be heading in. Were City about to fluff it again at the Tottenham Hotspur Stadium?
No. Vicario jostled with Ruben Dias from a corner with three minutes left, only able to push the ball down onto the ground. By the time it sprang back up off the turf, there was Nathan Ake to stab home a late and ugly but glorious winner for City.
Another season, another missed chance of cup silverware for Tottenham. Only the league is left now. They must recover fast from this body blow to give themselves any chance at all of success in that department.