Mason Mount missed in the shoot-out as Tottenham came from behind to dump Chelsea out and pile the pressure on Frank Lampard.
Cruising through Timo Werner’s first goal for the club, Lampard’s side shot themselves in the foot by coughing up a late Erik Lamela equaliser.
Until Lamela struck in the 83rd minute, it looked like Werner would show strikerless Spurs what money can buy in the transfer market.
With Harry Kane on the bench and Spurs no closer to signing another centre-forward, Mourinho chose to start this game without one. Chelsea’s £45m new boy Werner showed him just what he was missing to hit the opener.
But Spurs, who could not find a space in the squad for Dele Alli, dominated the second half and took it to penalties when Lamela struck.
That set things up for another Chelsea new boy, goalkeeper Edouard Mendy, to be the hero on his Blues debut.
But Mendy could not get near any of Tottenham’s spot-kicks – and it was Mount’s miss which ended up costing his side.
There was also a comedy moment when the home side temporarily went down to ten men when Eric Dier sprinted off for what looked like a toilet break.
But Mourinho ended up having the last laugh over Lampard after a brief touchline spat between the pair as Chelsea’s mixed start to the season continues.
Roman Abramovich has spent more in this window than any other but the Blues do not look like title contenders and this was a competition they hoped to go all the way in.
Spurs only got this far after receiving a bye because Leyton Orient were forced to forfeit their tie because of a Covid-19 outbreak.
But Mourinho got his excuses in early before the game even kicked off when he insisted his team’s fixture pile-up had already made the competition impossible to win.
With Spurs facing a lightning quick turnaround before Thursday’s Europa League clash with Maccabi Haifa, Mourinho made nine changes and reverted to a back three.
The visitors dominated from the off, with Callum Hudson-Odoi wasting an early chance to score before Werner broke the deadlock.
It was Spurs debutant Sergio Reguilon’s fault, losing the ball cheaply and then diving into a tackle he failed to win.
Cesar Azpilicueta made him pay, picking out Werner on the edge of the box, and the Germany star smashed it home through a crowd of bodies.
Chelsea then needed Kurt Zouma to get them out of trouble with a fabulous recovery tackle on Gedson after good work from Erik Lamela.
And things got testy when a disputed foul by Lamela sparked a touchline war of words between the two managers. Spurs enjoyed just 29% possession in the first half and only managed one shot on target, with Mourinho clearly expecting better.
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Whatever he said the break obviously had an impact as Serge Aurier picked out Reguilon and his rising drive was tipped over by Mendy.
But Werner could have killed it in the 72nd minute when substitute N’Golo Kante won the ball and Mason Mount fed him in a great position only for Lloris to save his shot.
Mount should later have played in Werner when the two found themselves bearing down on goal with only Dier for company, but the England defender made the block.
And Lamela then took advantage of some more dodgy Chelsea defending with six minutes to go score with a tap-in after three players failed to stop Reguilon’s cross.
That sent it to the lottery of penalties, and with a limping Werner opting not to take one, it was Mount’s miss that decided it.
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