Tottenham's Bobby Zamora scored in the first minute of extra time to send West Ham crashing out of the Carling Cup on Wednesday.
Zamora, who signed from Brighton in the summer, notched up his first goal for Spurs as the Premiership side marched into the fourth round.
But it was bitter disappointment for their Division One opponents, who had valiantly held the home team to 0-0 after full-time in a tense London derby.
The defeat also leaves new manager Alan Pardew still looking for his first win at West Ham.
Tottenham's joy was marred by a knee-ligament injury to Christian Ziege, who was starting his first game for nearly a year following a thigh problem.
Neither side could find the net in normal time, although Spurs were saved by the woodwork and a fine save from Kasey Keller.
Rob Lee saw his 38th-minute effort rebound off the post after being played in by Jermain Defoe, then it was Defoe who was denied by a Spurs goalkeeper Keller's good save after 65 minutes.
Richard Garcia also had a chance to nick it in injury time but hesitated in front of goal to allow Spurs to clear.
The closely contested clash was finally settled just 70 seconds into extra-time when Zamora held off Anton Ferdinand on the left edge of the box, to turn a low drive past England goalkeeper David James.
West Ham refused to give up just yet and, after 97 minutes, Hutchison forced another fine save from Keller with an angled drive.
But when Postiga almost scored his first goal for the club two minutes later, it seemed West Ham had run out of steam.
In the 102nd minute, Zamora nearly grabbed his second but James saved well.
More chances followed at both ends, but the Hammers were to leave empty-handed.