Mason Mount missed the final spot-kick as Tottenham beat Chelsea 5-4 on penalties to progress to the quarter-finals of the League Cup after a 1-1 draw.
Timo Werner’s first goal for Chelsea put Frank Lampard’s men in command against a much-changed Tottenham team playing the second of four games in eight days.
But Erik Lamela deservedly levelled for Spurs seven minutes from time and new Chelsea goalkeeper Edouard Mendy was unable to stop Eric Dier, Lamela, Pierre-Emile Hojbjerg, Lucas Moura and Harry Kane scoring from the spot.
Tammy Abraham, Cesar Azpilicueta, Jorginho and Emerson also converted their penalties as the first nine of the shootout were successful.
But Mount’s effort clipped the post to the delight of the watching Gareth Bale, who could be fit to feature in the last eight with the quarter-finals not till late December.
Mourinho claimed the fixture pile up gave him no choice but to prioritise Thursday’s Europa League tie against Maccabi Haifa given the financial incentive on offer for the club.
But despite making nine changes, he named a strong side, including captain Hugo Lloris, club record signing Tanguy Ndombele and new signing Sergio Reguilon on his debut.
Chelsea also handed a debut to Mendy and the early signs from the Frenchman were encouraging that he can solve the Blues’ problem position.
Lampard made eight changes, but Werner was one of those retained from the 3-3 draw at West Brom on Saturday and he took the opportunity to get his first goal for the club after a big money move from RB Leipzig.
Reguilon was twice at fault in the build up as he gifted possession to Azpilicueta and then dived in trying to block the Spaniard’s cross, which allowed the Chelsea captain to pick out Werner at the edge of the box to arrow a shot into the bottom corner.
Tottenham responded well to going behind as only a last-ditch intervention from Kurt Zouma denied Gedson Fernandes an equaliser.
Lampard had won his previous three meetings against his former manager Mourinho and the tensions between the two flared during the first-half as they exchanged angry words on the touchline.
On the field, Spurs were the better side as Mendy made important saves from Lamela and Reguilon either side of half-time.
Mourinho showed his intent by introducing Harry Kane from the bench with 20 minutes to go.
Moments later the Portuguese was marching down the tunnel after Dier as the defender made a dash to the dressing room before quickly returning.
Chelsea did not make the most of a brief period with an extra man as Callum Hudson-Odoi fired over and Werner’s fierce effort was saved by Lloris.
And the visitors were punished seven minutes from time when Lamela slotted home at the far post from Reguilon’s cross to send the game to a shootout and ultimately Spurs into the last eight.