Former Tottenham striker Jermain Defoe and ex White Hart Lane trainee Peter Crouch grabbed the goals in a 2-0 victory as Portsmouth nailed hapless Spurs even more firmly to the bottom of the Barclays Premier League.
Spurs, now without a win in six games, fell behind to a Defoe penalty in the 34th minute after Jermaine Jenas handled.
The visitors had a spot-kick appeal of their own denied by referee Mike Dean when Lassana Diarra, later sent off for two yellow cards, clearly appeared to handle substitute Aaron Lennon's 53rd minute cross.
And Spurs were buried by Crouch's header following Heurelho Gomes' parry of Armand Traore's 67th-minute shot.
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