Mason Mount missed the crucial spot-kick as Tottenham edged past Chelsea on penalties after a 1-1 draw to reach the Carabao Cup fifth round.
A total of nine penalties had been converted before Mount stepped up to take the 10th, but the England midfielder’s effort clipped the post and went wide.
Chelsea had dominated the first half and new signing Timo Werner netted his first goal for the club with a clinical finish into the bottom corner.
Spurs responded well after the break and debutant Sergio Reguilon’s side-footed effort from inside the area was pushed over the crossbar by Chelsea goalkeeper Edouard Mendy, who was also making his first appearance for his new club.
Jose Mourinho’s side got their rewards seven minutes from time when Spaniard Reguilon’s cross sailed through to the back post for Erik Lamela to coolly convert from six yards.
With no extra time played, the match went straight to penalties and Mount was the only player to miss.
Second-string Spurs advance
Spurs boss Mourinho seemed to dismiss the competition before the game, saying the sheer number of fixtures his side face means he has to prioritise the Europa League as the money from it is “very important”.
An arduous schedule sees Spurs in the middle of a run of four games in the space of eight days.
After drawing with Newcastle on Sunday and getting past Chelsea on Tuesday, further matches follow on Thursday, against Maccabi Haifa in Europa League, and on Sunday, when they meet Manchester United in Premier League.
But Mourinho will be delighted at scraping through against his former club, where he had two spells as boss and won three Premier League titles.
Mourinho was brought in as Mauricio Pochettino’s replacement last November with the aim of securing a long-awaited trophy – their victory in this competition back in 2008 being their most recent silverware.
The returning Gareth Bale remains unavailable through injury but fellow new boy Reguilon, whose mistake led to Chelsea’s goal, improved as the game wore on, showcasing his electric pace and ability to create a goal.
The wing-back was a constant outlet down the left in the second half and it was he who picked out Lamela for the leveller.
Eric Dier, Lamela, Pierre-Emile Hojbjerg, Lucas Moura and Harry Kane all converted their spot-kicks to help Tottenham through to the next round.
More to follow.
Line-ups
Tottenham
- 1Lloris
- 25TangangaBooked at 61minsSubstituted forKaneat 70′minutes
- 4Alderweireld
- 15Dier
- 24AurierBooked at 59mins
- 30Carvalho FernandesSubstituted forHøjbjergat 63′minutes
- 17Sissoko
- 28Ndombele
- 3Reguilón
- 11Lamela
- 23BergwijnSubstituted forLucas Mouraat 76′minutes
Substitutes
- 2Doherty
- 5Højbjerg
- 6D Sánchez
- 10Kane
- 12Hart
- 27Lucas Moura
- 33Davies
Chelsea
- 16Mendy
- 28Azpilicueta
- 14Tomori
- 15Zouma
- 21ChilwellSubstituted forEmersonat 66′minutes
- 5JorginhoBooked at 83mins
- 17KovacicBooked at 45minsSubstituted forKantéat 70′minutes
- 20Hudson-Odoi
- 19Mount
- 11Werner
- 18GiroudSubstituted forAbrahamat 76′minutes
Substitutes
- 1Arrizabalaga
- 7Kanté
- 8Barkley
- 9Abraham
- 24James
- 29Havertz
- 33Emerson
Live Text
Match ends, Tottenham Hotspur 1(5), Chelsea 1(4).
Penalty Shootout ends, Tottenham Hotspur 1(5), Chelsea 1(4).
Penalty missed! Still Tottenham Hotspur 1(5), Chelsea 1(4). Mason Mount (Chelsea) hits the left post with a right footed shot.
Goal! Tottenham Hotspur 1(5), Chelsea 1(4). Harry Kane (Tottenham Hotspur) converts the penalty with a right footed shot to the bottom right corner.
Goal! Tottenham Hotspur 1(4), Chelsea 1(4). Emerson (Chelsea) converts the penalty with a left footed shot to the bottom left corner.
Goal! Tottenham Hotspur 1(4), Chelsea 1(3). Lucas Moura (Tottenham Hotspur) converts the penalty with a right footed shot to the bottom left corner.
Goal! Tottenham Hotspur 1(3), Chelsea 1(3). Jorginho (Chelsea) converts the penalty with a right footed shot to the bottom right corner.
Goal! Tottenham Hotspur 1(3), Chelsea 1(2). Pierre-Emile Højbjerg (Tottenham Hotspur) converts the penalty with a right footed shot to the bottom left corner.
Goal! Tottenham Hotspur 1(2), Chelsea 1(2). César Azpilicueta (Chelsea) converts the penalty with a right footed shot to the bottom left corner.
Goal! Tottenham Hotspur 1(2), Chelsea 1(1). Erik Lamela (Tottenham Hotspur) converts the penalty with a left footed shot to the bottom left corner.
Goal! Tottenham Hotspur 1(1), Chelsea 1(1). Tammy Abraham (Chelsea) converts the penalty with a right footed shot to the bottom left corner.
Goal! Tottenham Hotspur 1(1), Chelsea 1. Eric Dier (Tottenham Hotspur) converts the penalty with a right footed shot to the bottom left corner.
Penalty Shootout begins Tottenham Hotspur 1, Chelsea 1.
Second Half ends, Tottenham Hotspur 1, Chelsea 1.
Foul by N’Golo Kanté (Chelsea).
Tanguy Ndombele (Tottenham Hotspur) wins a free kick in the defensive half.
Attempt blocked. Timo Werner (Chelsea) right footed shot from the centre of the box is blocked.
Foul by N’Golo Kanté (Chelsea).
Tanguy Ndombele (Tottenham Hotspur) wins a free kick on the right wing.
Attempt blocked. Erik Lamela (Tottenham Hotspur) left footed shot from the right side of the box is blocked. Assisted by Tanguy Ndombele.
