Defeat to Derby could prove to be Jose Mourinho’s point of no return

Let's not forget that the great Manchester United, for all their storied history and 4.9-star apps, have had nights like this before.

As their supporters filtered out of Old Trafford following Tuesday night's miserable shoot-out defeat to Derby, some might have recalled a similar League Cup occasion almost exactly 11 years ago. Coventry City - then of the Championship - took on a patchwork United side on their own turf in September 2007, beating them courtesy of two Michael Mifsud goals. As standalone games, there are obvious parallels between both defeats. But given wider context, they couldn't be further apart. At the time of the Coventry defeat, United were reigning Premier League champions and had reached a Champions League semi-final the previous season. Cristiano Ronaldo and Wayne Rooney, two of the most exciting young attackers in world football, were developing at breakneck speed, supported by crucial new signing Carlos Tevez. There was an expectancy that United would retain their title that season; a belief that they could win their third European Cup. Sure enough, they went on to claim both. Few, if any, of the club's supporters harbour hopes that this current crop of players can emulate those achievements. Eight points have already been lost in the league and the possibility of United getting the better of the continent's top clubs in the Champions League seems out of the question. Instead, what happened against Derby serves as yet another reminder of how things could become even worse before the good times return to Old Trafford. Jose Mourinho is at the centre of this negative spiral, with Tuesday's shambolic cup exit doing little to dampen the feeling that his departure is becoming inevitable. As someone who built his glowing CV on having absolute control, Mourinho is increasingly losing his grip on the all-important narrative. The continuing circus surrounding his relationship with Paul Pogba is the most telling sign of this, though other things - his recent press conference performance, for example - also imply that Mourinho himself knows he is floundering in the job he courted for so long. Every game United fail to win - every insipid display where players signed for enormous fees look more like individuals than a collective force - only throws up more questions. Defensive frailties were exposed in the defeat to Brighton last month, but the primary concern is Mourinho's inability to get the best out of the squad's attacking talent. Alexis Sanchez has drifted since his arrival from Arsenal in January, while Anthony Martial and Marcus Rashford have been shunted into wide positions to accommodate Romelu Lukaku as the No.9. There are mitigating circumstances, of course. For the first time in 17 years, Mourinho is operating without the help of Rui Faria following his assistant's departure in the summer. Some of his complaints about United failing to deliver in the transfer market have also carried weight. But despite this weak explanation for how United reached this point, Mourinho's stint as manager has accrued more damage than will likely prove to be reconcilable. The embarrassment of a defeat to Derby may not hurt United too much in the long-term, but it only adds to the sense that Mourinho has already passed the point of no return.