As far as derby defeats go, this one is as untimely as they come for Pep Guardiola and Manchester City. Losing to Manchester United is tough to take at the best of times for anybody associated with City, but this will really sting.
From 10 consecutive victories to start the season it is now six games without a win for Guardiola’s project. It is the worst run of his managerial career, and the first signs that his methods are not working.
That’s not to say they won’t work, or that his time at City is destined to fail, but it is a fact that he has never gone through a barren period like this.
There are certainly reasons why City has not been at its best throughout the month of October, there are reasons why the club has come away from certain games with one point rather than three, and there are reasons why it lost at Old Trafford on Wednesday.
But how long until the reasons become excuses?
It is still too early to talk of a crisis at the Etihad Stadium but this is undoubtedly a very disappointing period given the heights Guardiola is expected to reach.
Yes, City showed great character in the 3-3 draw at Celtic and could have easily won the game in the final 20 minutes. It was outplayed, pure and simple, by Tottenham a few days later. Those were two extraordinary games given the atmosphere in Glasgow and the intense pressure in London.
The home draw against Everton was unfortunate, given City missed two penalties and forced two further world-class saves from the opposition goalkeeper. The team then played well at Barcelona until Claudio Bravo’s red card induced a humbling 4-0 defeat.
But, if those four results could be explained away, the draw against Southampton was worrying given City did not create the type of chances that it mustered against Everton. City's buildup play was slower and, bar the defeat at Spurs, it was its worst performance of the season.
Still, the Blues entered the derby in higher spirits than their local rivals given United’s own – and more chaotic – struggles. Jose Mourinho is supposed to have shocked his players with his hands-off approach to training, and his comments about living in a Manchester hotel were interpreted as those of a man at the end of his tether already.
Guardiola, despite previous results, came into this game as very much the man with the plan. But it is Mourinho who emerges victorious from this decisive clash against his old rival and the one who will sleep soundly tonight.
Such was his plight the Portuguese felt he needed to pick a full-strength side for this encounter and that is one factor in their victory. Guardiola made a number of changes to his lineup and, although it involved several senior players, it was by no means as strong as United’s XI. Still, the Blues shaded a poor first half – with youngster Aleix Garcia and Fernando looking impressive - but they were overcome after the break as United upped the tempo.
Paul Pogba, Ander Herrera and Michael Carrick have not been United’s first-choice midfield so far this season, but it should be. They have the perfect balance and it is no surprise they eventually wrested control of the game from a midfield pairing of the young Garcia and Fernando, who is very much Fernandinho’s understudy.
Most concerning for City, however, is how quickly it all seemed to unravel. There was none of the fight or intensity that has characterized the vast majority of its games this season, even some in this fallow month of October.
Raheem Sterling and Sergio Aguero were thrown into the fray but made little impact as United retreated and held on for a victory which will surely do wonders for the mood around Old Trafford – not to mention Mourinho’s hotel room.
But Guardiola will go back to his city center apartment with plenty to ponder. He has supreme confidence in his approach to football management and rightly so: as he has pointed out recently, it has garnered 21 trophies in seven years.
But this is the first indication that things aren’t working. He has simply not had a run of results like this, no matter if some of the performances have deserved better. The question is whether it will be enough to do the unthinkable and shake his unshakeable confidence.
Most likely it will not, but West Brom is not the ideal place to go when you are struggling to create chances, and it’s Barcelona after that.
This run could very easily get worse before it gets better. There is every chance it will get better, and that Guardiola will enjoy a similar level of success to that which he enjoyed in Barcelona and Munich.
But who can be sure? Perhaps not even Guardiola himself.