Liverpool made it into the last four of the Carling Cup with a 4-3 penalty shoot-out victory over Tottenham after the sides were tied 1-1 after 120 minutes.
Jermain Defoe gave Spurs the lead their dominance - if not their finishing - had deserved after 107 minutes of wasted chances, only for Frederic Kanoute to inexplicably handle a harmless cross in his own box.
Florent Sinama-Pongolle swept home the spot-kick and forced a tie that Tottenham should have comfortably ended in normal time into the lottery of a penalty shoot-out.
With the scores tied at 2-2, Kanoute was then the first player to miss for Tottenham and though Darren Potter had his effort saved by home goalkeeper Paul Robinson, Michael Brown gave Liverpool the advantage when he skied his effort over the crossbar.
And it was left to Sinama-Pongolle, the 20-year-old, to fire his penalty to Robinson's left - the opposite corner to his extra-time spot-kick - and propel Liverpool into a semi-final clash with Watford.
In truth it was little more than Tottenham deserved. They had spent all of normal time wasting a glut of chances, with Rohan Ricketts and Robbie Keane the chief culprits.
Liverpool's reserves clung on force extra-time and the longer Tottenham went without scoring and the more possession they squandered, the brighter Rafael Benitez's youngsters grew.
The Spaniard brought in Zak Whitbread, Stephen Warnock and David Raven alongside Stephan Henchoz in an inexperienced defence which was nearly breached after just five minutes.
Reto Ziegler picked out Kanoute in the box and the Mali international turned on a sixpence, only for his shot to deflect off the crossbar and into the stand.
The chances were coming thick and fast for Tottenham but Kanoute scuffed a volley wide and Ziegler should have done better than to fire into the side-netting.
Kanoute then turned provider from the right, finding Ricketts unmarked in the centre of the Liverpool box with a perfect cross but his header was glanced horribly wide.
Liverpool were gaining heart from their own stubborn resistance but could do little to stem the tide, surviving only through Tottenham's impotence in the final third.
When Ziegler whipped over a low cross from Tottenham's sixth corner of the half all it needed was a touch. None came.
It fell to Robbie Keane at the far post but he was denied by the first of two brilliant reflex saves from the swiftly advancing Jerzy Dudek.
When the players emerged for the second half, little had changed. Keane hit the side-netting with an open goal gaping - the worst miss of the lot - and when Kanoute presented the Republic of Ireland striker with a chance to make amends five minutes later, Dudek somehow tipped his volley over the crossbar.
Defoe, who had been sat watching on the bench, was sent to warm up down the touchline. Head coach Martin Jol had seen enough and the England striker was introduced for Ricketts with 25 minutes remaining.
Defoe was given little chance to shine as Tottenham remained sloppy in possession and they were beginning to tread a fine line - wasteful up front as Liverpool increasingly tested them at the back.
With 11 minutes remaining Anthony Gardner was lucky to escape a red card when, as the last man back, he virtually rugby tackled Sinama-Pongolle to the ground.
Liverpool, furious at referee Neale Barry, responded best and when the whistle blew for extra-time, it was Tottenham who were clinging on. The White Hart Lane crowd responded with a chorus of boos.
John Welsh, a second-half replacement for Neil Mellor, shaved the outside of the post at one end before Raven, making his first start, produced a perfectly-timed tackle to stop a charging Defoe.
After the turnaround, when Kanoute picked out Defoe, the game was seemingly won. But Kanoute then gifted Liverpool a chance to level from the spot, and ultimately win the match in the same manner.
Victorious Liverpool manager Rafael Benitez refused to rule out bringing back
his top players for the Carling Cup semi-final against Watford.
'We have a lot of tired players and we will wait and see nearer the time,'
'It depends on the players at the time of the games but I still have the same
idea as when I arrived. My priorities are the Premier League, Champions League,
FA Cup and Carling Cup.
'I don't want to win the Carling Cup and finish 10th in the Premiership. I
want to finish in the top four and win more things.'
Benitez was delighted with the spirit shown by his kids, particularly in the
He added: 'I was not surprised. For the future of the club it is important to
have young players playing this kind of game. It will give them more experience
and they will remember this situation.'
Benitez was also pleased with Pongolle's contribution from the penalty spot.
Liverpool are in the midst of a striker crises but Pongolle's two penalties will
give Benitez more options.
He added: 'It was important for him to score. Against Arsenal Neil Mellor
played well and now Pongolle has scored two important goals. It gives me more
options in attack now.'
Beaten Spurs coach Martin Jol will forgive striker Kanoute but blamed him for
Jol could not understand why his striker handled the ball four minutes from
the end of extra-time with Spurs leading 1-0 and then was not cool enough to
convert his spot-kick in the shoot-out.
Jol said: 'The defeat hurts but I still cannot understand why he did it.
There was no pressure on him. How can you handle it?
'Fredi is too disappointed. But he knows he should not do it. We have to move
on because we need Fredi. Of course, it is not unforgivable but Fredi has to go
on. It cost us dearly. At every club there is a person like that but I can't
believe we are still doing those sort of things.
'He was not cool with his penalty. It is about coolness. But I know Fredi and
in training he is always scoring penalties.'
Failure to take their chances, and Spurs had numerous ones to finish off
Liverpool, was also a problem for Jol.
'We should have been two or three up. We did not punish them. In the
first-half everybody could see there was no problem for us. They played a lot of
youngsters but we did not finish our chances. We punish ourselves all the time.
the difference between success and failure is too thin.'