Florent Sinama Pongolle was Liverpool's match-winner as the young Frenchman's vital penalty kick sent the Reds into the semi-finals of the Carling Cup.
Despite making wholesale changes to the side that beat Arsenal 2-1 on Sunday, Rafael Benitez's second string side still had enough quality to make the last four of the competition after the game went to a penalty shoot-out.
Frederic Kanoute and Michael Brown were the villains for the home side as they missed from the spot and it was left to Pongolle to send Liverpool through to a semi-final clash against Watford.
Tottenham started strongly and Kanoute could have broken the deadlock after just six minutes.
Reto Ziegler's pass picked out the Mali international inside the box and Kanoute fired a powerful close-range shot which struck the top of the crossbar.
Spurs continued to press and Ziegler managed to weave his way into the area in the 16th minute, but drilled his shot into the side-netting.
Kanoute turned provider once again for Tottenham four minutes later when he beautifully picked out Rohan Ricketts inside the box.
Ricketts found himself completely unmarked just five yards from goal, but with the goal at his mercy he flashed his header wide of the post.
And the young winger had another golden chance to get his name on the scoresheet in the 35th minute when the Liverpool defence failed to clear the ball.
The ball fell nicely to him on the edge of the box, but he fired a powerful drive wide of Jerzy Dudek's goal.
It was all one-way traffic and Robbie Keane will still be wondering how he didn't break the deadlock in the 38th minute.
Noe Pamarot's ball across goal fell to the Republic of Ireland international whose close-range left-foot shot was superbly beaten away by Dudek diving away to his right.
Keane must have thought it was not going to be his night as he spurned another glorious chance in the 53rd minute.
Dudek failed to deal with a high cross into the penalty area and the ball fell kindly to Keane, but he somehow managed to strike the ball into the side-netting with the goal gaping.
And the pain continued for the Spurs hit-man on the hour when Kanoute picked him out only for his close-range shot to be finger-tipped over the bar by Dudek.
Liverpool had to wait until the 72nd minute before creating their first opportunity of the game. Substitute Mark Smyth whipped in a low shot which Paul Robinson saved diving low to his left.
Tottenham defender Anthony Gardner was lucky to stay on the pitch in the 78th minute when he prevented Pongolle from having a clear run on goal.
But the referee infuriated the Liverpool players and supporters when he only pulled out a yellow card.
John Welsh could have made a name for himself five minutes into extra-time when he tricked his way into the Spurs box, but curled his shot inches past the post.
And Liverpool were made to pay as Tottenham finally broke the deadlock just two minutes into the second period of extra-time.
Kanoute broke free down the right and played the perfect ball back for Jermain Defoe who made no mistake striking the ball into the back of the net.
However, with just four minutes remaining Liverpool snatched an equaliser. Robinson superbly pushed Pongolle's close-range header over the bar but from the resulting corner, Kanoute was adjudged to have handled the ball inside the box and Pongolle struck the resulting spot-kick into the corner of the net.
In the penalty shoot-out Brown and Kanoute both missed from the spot and Pongolle made no mistake sliding the ball into the corner of the net for the vital winner.