Match ends, Colchester United 0(4), Tottenham Hotspur 0(3).
League Two Colchester United produced a huge upset as they beat Premier League Tottenham on penalties to reach the Carabao Cup fourth round.
The Essex side - the lowest-ranked team left in the competition - frustrated last year's semi-finalists throughout the 90 minutes and won a dramatic shootout after Christian Eriksen and Lucas Moura missed from the spot.
After Eriksen's first kick of the shootout was saved by Dean Gerken, the hosts looked to have wasted their advantage when Jevani Brown tried an audacious 'Panenka' effort, which was so weak that Paulo Gazzaniga was able to abort his dive, stand up and punch the ball to safety.
But when Moura smashed Tottenham's fifth effort against the bar, Tom Lapslie stepped up to send Colchester into the last 16 for the first time in 44 years and prompt wild celebrations.
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The biggest upset of Pochettino's career
Tottenham manager Mauricio Pochettino has yet to win a major trophy during his managerial career, despite an encouraging season in 2018-19 which featured an appearance in the Champions League final and making the last four of this competition.
But his wait for a trophy will go on after the biggest shock he has experienced as a manager.
The Argentine had taken charge of 18 domestic cup ties against lower-ranked opponents since arriving in England with Southampton in 2013 and had never lost.
Spurs are on a gruelling run of seven games in 21 days but they could hardly blame tiredness for this result, with Pochettino making 10 changes from their defeat at Leicester - only keeper Gazzaniga kept his place.
There was a first outing of the season for out-of-favour Eric Dier, a return from injury for Dele Alli and debuts for 20-year-old centre-back Japhet Tanganga and 17-year-old forward Troy Parrott, but none pressed their claims to break into their manager's first-choice XI.
This defeat will only add to the sense of uncertainty around the club - BBC Radio 5 Live summariser Don Hutchison said before the game there was an "undercurrent of frustration" surrounding Pochettino and that it was hard to "see where the club is going".
Four wins in their past 17 matches suggests something is not quite right.
And what is going on with their away form? They are winless in all five games on the road this season, conceding two goals on four occasions and - most worryingly - now suffering an embarrassing exit from the EFL Cup.
Two down, how many to go?
Colchester had already produced one significant upset this season, winning on penalties at Crystal Palace in the second round.
Adding the scalp of Tottenham - who were eliminated by a team from a lower division in this competition for the first time since Grimsby achieved the feat in 2005-06 - means Colchester are the first side from outside the top flight to win shootouts against two top-tier sides in the same League Cup campaign since Bradford City in 2012-13. They went on to reach the final that season.
The bigger clubs routinely use this competition as a testing ground for squad members and younger players and, after beating a side ranked 70 places above them, John McGreal's men are unlikely to fear whoever they face when Wednesday's fourth-round draw is made.
They held their own in this game, despite Tottenham having 75% of possession and 19 shots. In truth, Colchester were rarely under serious pressure, with only four of those efforts on target.
Kyle Walker-Peters' cross-shot crashed against the post early in the second half but, as the game approached full-time and Pochettino brought on Son Heung-min, Eriksen and Lamela to add to the attacking power of Alli and Moura, Colchester looked as likely to break the deadlock.
As it turned out, they did not need to.
'It's worrying times for Tottenham' - what they said
Tottenham boss Mauricio Pochettino: "Colchester made a fantastic game, it was difficult. We are so disappointed we could not score in 90 minutes.
"They beat Palace on penalties too, that can happen. That's the beauty of the competition, always something can happen.
"We wanted to go further but we are out."
Colchester manager John McGreal: "It's a fantastic night for the players and the club and even the staff.
"When you are coming up against the players of Tottenham's calibre, sometimes on these type of nights you need a bit of luck.
"It's a great occasion for us."
Former Bolton manager Owen Coyle on BBC Radio 5 Live: "It's worrying times for Tottenham. They are already 10 points adrift in the league and so that is a huge ask. Then they ask can we win a trophy? This one has gone now.
"I do think they have to find a way to win games quickly. Mauricio Pochettino is a wonderful manager but a lot of those players have to stand up and take accountability."
Tottenham will aim to improve on a faltering start which has earned them eight Premier League points from their opening six games - and left them in seventh place - when Pochettino's former club Southampton travel to north London on Saturday. Colchester travel to Macclesfield on Saturday hoping for a win that could take them into the League Two play-off places.
- 2JacksonSubstituted forCowan-Hallat 50'minutesBooked at 56mins
- 24StevensonSubstituted forNorrisat 78'minutes
- 26GambinSubstituted forBrownat 68'minutes
- 6D Sánchez
- 39TangangaSubstituted forSon Heung-Minat 66'minutes
- 29SkippSubstituted forLamelaat 78'minutes
- 27Lucas Moura
- 52ParrottSubstituted forEriksenat 66'minutes
- 7Son Heung-Min
- Jarred Gillett
- Shots on Target
Penalty Shootout ends, Colchester United 0(4), Tottenham Hotspur 0(3).
Goal! Colchester United 0(4), Tottenham Hotspur 0(3). Tom Lapslie (Colchester United) converts the penalty with a right footed shot to the bottom left corner.
Penalty missed! Still Colchester United 0(3), Tottenham Hotspur 0(3). Lucas Moura (Tottenham Hotspur) hits the bar with a right footed shot.
Goal! Colchester United 0(3), Tottenham Hotspur 0(3). Paris Cowan-Hall (Colchester United) converts the penalty with a right footed shot to the top right corner.
Goal! Colchester United 0(2), Tottenham Hotspur 0(3). Son Heung-Min (Tottenham Hotspur) converts the penalty with a right footed shot to the bottom left corner.
Penalty saved! Jevani Brown (Colchester United) fails to capitalise on this great opportunity, left footed shot saved in the top centre of the goal.
Goal! Colchester United 0(2), Tottenham Hotspur 0(2). Erik Lamela (Tottenham Hotspur) converts the penalty with a left footed shot to the top right corner.
Goal! Colchester United 0(2), Tottenham Hotspur 0(1). Frank Nouble (Colchester United) converts the penalty with a right footed shot to the centre of the goal.
Goal! Colchester United 0(1), Tottenham Hotspur 0(1). Dele Alli (Tottenham Hotspur) converts the penalty with a right footed shot to the bottom left corner.
Goal! Colchester United 0(1), Tottenham Hotspur 0. Luke Norris (Colchester United) converts the penalty with a right footed shot to the bottom left corner.
Penalty saved! Christian Eriksen (Tottenham Hotspur) fails to capitalise on this great opportunity, right footed shot saved in the bottom left corner.
Penalty Shootout begins Colchester United 0, Tottenham Hotspur 0.
Second Half ends, Colchester United 0, Tottenham Hotspur 0.
Eric Dier (Tottenham Hotspur) wins a free kick in the defensive half.
Foul by Luke Norris (Colchester United).
Attempt saved. Eric Dier (Tottenham Hotspur) right footed shot from outside the box is saved in the centre of the goal. Assisted by Christian Eriksen.
Attempt saved. Lucas Moura (Tottenham Hotspur) header from the centre of the box is saved in the centre of the goal. Assisted by Son Heung-Min.
Attempt missed. Courtney Senior (Colchester United) left footed shot from outside the box is close, but misses to the right. Assisted by Tom Eastman.
Foul by Kyle Walker-Peters (Tottenham Hotspur).