Both sets of players had combined for an immaculate first nine penalties before Mason Mount's effort – Chelsea's fifth – clipped the outside of the post. No goalkeeper got a hand to any of the 10 efforts, but perhaps Hugo Lloris' full-blooded dive to his right forced Mount to go wider that he would have liked.
The sides were even after 90 minutes. Timo Werner scored his first goal for Chelsea to give them a lead in the 19th minute, one which they held until 83 when Erik Lamela pounced to put Tottenham back on level terms.
The match was always going to feature tweaks given we are not long from the weekend, where both sides registered unfulfilling draws. And though this competition represents the best chance at silverware to both sides, there was an air of inconvenience at the fixture from Spurs point of view, even if this London Derby has a recent history of being high quality with welcome amounts of bad blood.
Nevertheless, Mourinho was joyous at the end of the match, dancing down the tunnel while Frank Lampard, faced scrunched, consoled his players and congratulated their opponents. Another plus for Mourinho was the fact they have emerged from the second match of four in the space of eight days with no new injuries. An absurd schedule that now at least has brought some cheer.
Spurs made nine changes to the XI that felt robbed by Sunday’s late penalty against Newcastle. Harry Kane started on the bench, with an eye on Thursday’s last Europa League qualifier against Maccabi Haifa, before Sunday’s return to the Premier League against top-four rivals Manchester United.
Despite the need for first-team bodies, Dele Alli was once again left out of the match day squad. Though it is unclear where he might go, with Paris St Germain the main suitors, it looks certain that his days in north London are number. And as one Spurs career seems to be ending with a whimper, another began in a similar ignominious fashion.
Debutant Sergio Reguilon, signed from Real Madrid, was at fault for Chelsea’s opening goal: losing possession to César Azpilicueta and then two passes later sat down by his compatriot, who took his time to find Werner on the edge of the box.
It is a moment that won’t fill Spurs fans with particular joy, even though the majority will know the 23-year old full-back is highly regarded for his work going forward than towards his own goal. By contrast, the opposition left-back Ben Chillwell, on his first start for Chelsea, was enjoying a good deal of space down his flank t showcase his attacking threat.
Another new face was in the visitor goal as Edouard Mendy was given his debut by Lampard, and also provided some good early signs. He made himself big when Gedson Fernandes approached him one-to-man - a perfect Kurt Zouma tackle snuffed out that danger.
Then, 10 minutes before half-time, he strong save with his right foot preserved Chelsea’s 1-0 lead at the break.The former Rennes keeper was called into action five minutes into the second period, this time to thwart fellow newbie Reguilon who, perhaps, would have beaten him if he was not so desperate to make amends for the earlier error. A more controlled finish than the thwack straight at Mendy would have almost certainly yielded a better outcome. It cued up a period of dominance for the hosts that, in turn, saw Kane thrown on with 20 minutes to go, with Spurs adjusting to a more recognisable 4-3-3.
Naturally as they pushed, Chelsea found more joy, and there was a moment on 77 minutes when Eric Dier ran off the field, closely followed by Mourinho, and Callum Hudson-Odoi should have profited from the man advantage. But after Dier answered nature’s call, Lamela answered Spurs.
This time, Reguillon did get his redemption, taking down a cross-field pass from Toby Alderweireld, moving onto his weaker right-foot and crossing to the far post. Lamela, lurking, reacted quickest as the ball dropped into his path, firing past Mendy from eight yards with seven minutes of normal time still to play.
With no extra time and penalties done in regulation, Spurs can immediately turn their thoughts to Thursday. For Mourinho, he will be eyeing up a fifth league cup trophy. It may not be a marquee competition, but he knows as well as anyone that it helps to cultivate a winning habit. Judging by the performance of his side here to turn this match around, he may not be far off.