Aspirations of a second Carabao Cup title in three seasons ended prematurely as Manchester United fell to a bizarre 4-3 defeat against Tottenham Hotspur in North London.
The Reds came into the fixture on a high following a memorable derby day victory against Manchester City after the hard-fought Europa League beating of Viktoria Plzen.
Keen to maximise his squad, Ruben Amorim made five changes from the weekend fixture, with Marcus Rashford again absent and Alejandro Garnacho returning to the bench.
“I chose the players that looked ready to cope with the demands of playing a strong game,” the former Sporting chief advised Sky reporters before kickoff.
Amad Diallo, the star of the 195th Manchester meeting, was rested alongside Andre Onana and Kobbie Mainoo as the Portuguese tactician attempted to utilise his squad.
Ultimately, vulnerability was again the common denominator, as a calamity of defensive errors and a series of unforgettable goalkeeping moments gifted their hosts a semi-final spot.
Manchester United continue to endure their London hoodoo
The September meeting began with a counterattacking Spurs goal after three minutes, and the home side raced out of the blocks, attempting to replicate their antics.
Despite enduring criticism, Ange Postecoglou has remained committed to playing an attack-first high-lined mentality.
His intentions were clear after five minutes, with his entire team sitting on the halfway line to defend a deep United free kick.
But, as has been the case in recent weeks, Amorim has installed a structure within this group, and the visitors comfortably repelled an early onslaught.
With ten minutes played, the contrast from the league meeting was already evident, and despite the early days, this Manchester United side is starting to look like a well-coached football team.
Comfortable in defence, calculated in transition, and calm in possession, the newly arrived Portuguese coaching team deserves ample credit for the effectiveness of their approach in a short period.
But their journey is still at an early stage, and the vulnerability of this squad is undeniable.
Spurs opened the scoring against the run of play after 15 minutes through Dominic Solanke. Altay Bayindir failed to deal with a long-range Pedro Porro effort, palming his effort directly to the feet of the onrushing attacker.
Christian Eriksen made a rare start on his return to North London, and his influence on the ball was a constant threat.
He twice tested Fraser Forster with long-range efforts after 20 minutes before Dejan Kulusevski forced a fine save from Bayindir.
Despite trailing after half an hour, Amorim’s side controlled the game with sustained possession and attractive interplay. The issue, as has often been the case, was a lack of a killer touch in the final third.
Spurs retreated further into their half and remained content to battle attacks while utilising their blistering pace in transition.
The back-and-forth encounter made for an entertaining watch, but the home side was visibly tiring through an amalgamation of high-pressing and endless breakaway attempts.
Frustratingly, amidst the frantic play, a demoralised Victor Lindelof left the field with injury. Like Mason Mount, the Swedish international has endured a traumatic period with setbacks and sat on the floor in clear discomfort.
Jonny Evans, also returning from a spell on the sidelines, was introduced for his first appearance since the 1-1 draw with Ipswich in November.
United continued to pour forward and impress in possession, but a wall of white met their efforts in attack. John Brooks called time on the opening 45 with Solanke’s goal the difference between the sides.
Let the madness begin
The teams remained unchanged after the break, and play began just as it did in the first, with Spurs bursting out of the blocks.
First, a routine delivery into the area was poorly cleared by Lisandro Martinez into the path of Kulusevski, with the Swede smashing home his side’s second within a minute of the restart.
Much to the dismay of a visibly distraught Amorim, Solanke netted his second and Spurs third after 54 minutes, having latched onto a long ball before easily coasting past Martinez and Evans.
Like the first, both goals were avoidable and left the Portuguese touchline bemused at the jeopardy in their backline.
Joshua Zirkzee, Mainoo and Amad were introduced immediately afterwards, and the tone of the fixture bizarrely shifted.
Within minutes, the Dutchman came close to reducing the deficit with a fine header but was denied by the fingertips of Forster.
Astonishing, the veteran keeper then handed United a lifeline seconds later. Bruno Fernandes intercepted his lacklustre pass and laid off to Zirkzee for the easiest of tap-ins from two yards.
The 36-year-old shot-stopper was visibly shaken and dallied on the ball six minutes later, allowing the onrushing Amad to deflect his attempted clearance into the net.
United had drawn blood and introduced the flair and tenacity of Garnacho with 20 minutes to play in an attempt to complete a startling comeback.
From here, it was wave after wave of Red assault with a sense of familiarity building. Spurs were numb, and their guests were intent on delivering a fatal blow.
Noussair Mazraoui came close following fine work from Fernandes before Diallo fired a rasping effort from distance, forcing the most unorthodox of clearances from a shell-shook Forster with ten to play.
Extraordinarily, with all the play running towards an inevitable equaliser, a Heung-Min Son corner kick found its way directly past an impeded Bayindir with two minutes of regulation to play.
With VAR unavailable in the competition, the furious Turkish keeper received a yellow card for his protests as Brooks waved away a combined United plea.
Evans did head a third for United in the fifth minute of injury time. But the damage of yet another set-piece capitulation proved the end of a stirring comeback as Amorim embraced Postecoglou in defeat.
Historically, this fixture provides goals, with an average of 2.86 throughout the previous 21 meetings. Once more, it did not disappoint. As always, plenty of questions still require answers within the Old Trafford squad, with their head coach learning as he works.
He will have two days to prepare for a trio of fixtures in a congested Nine-day schedule, including home ties with Bournemouth and Newcastle and a trip to Wolves.
What are your takeaways from another London defeat for Manchester United?
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