Former Tottenham Hotspur striker Jermain Defoe and ex White Hart Lane trainee Peter Crouch grabbed the goals as Portsmouth ensured Spurs stayed at the bottom of the Barclays Premier League.
Spurs, now without a win in six league matches, 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.
Defoe came close to damaging the club who let him go in the first two minutes. Crouch's pass sent strike partner Defoe scampering clean through the middle to drill past goalkeeper Gomes - but the flag was raised for an obvious offside.
Campbell did not know whether to head or kick clear from Bentley's bouncing cross - and, in the end, did neither. Luckily for Pompey no Tottenham player was near enough to take advantage.
Defoe tried to find another way through in the 10th minute and although he was crowded out by a gang of Spurs' defenders the ball ran loose to Richard Hughes, whose fierce 20-yard shot was repelled by Gomes.
goalkeeper's swerve
Defoe brought another save out of Gomes before the agile Brazilian snatched the ball off Crouch's head after Pompey left-back Nadir Belhadj made a probing run and dangerous cross.
Little won a corner on the right off Gilberto and sent over the flag-kick for Crouch to use his height and nod narrowly over.
Soon after another Little corner was cleared only as far as Hughes on the edge of the area - and the midfielder hit a cracking volley which Gomes did well to keep out.
James finally had a shot to save in the 26th minute but it was a tame effort by Jamie O'Hara, who should have done much better from a central position 14 yards out.
As James carried the ball away, Jonathan Woodgate bumped into him from behind and was booked, caused by the goalkeeper's swerve before kicking clear.
O'Hara was booked in the 33rd minute for a foul on Little, who swept the free-kick into the area where Jermaine Jenas was adjudged by referee Mike Dean to have handled the ball.
fearsome drive
But that did not worry Defoe, who stepped up to bury the spot-kick past Gomes and, sportingly, decided not to celebrate in front of his former Tottenham fans.
The home fans' mood was lifted further with the unmarked Pavlyuchenko's reaction to a perfect O'Hara pass five minutes before the break. The Russian spun away from the flight of the ball, looking completely lost.
Winger Lennon's pace and guile looked a bonus and he fed Bentley to shoot not far off target before Gomes made another good stop at the other end from Traore.
With Bent still on the bench, Tottenham were denied what looked a clear penalty in the 53rd minute when Diarra appeared to handle Lennon's cross from the left.
Referee Mike Dean was unmoved though, and Portsmouth's luck was in.
Tottenham were having more of the match and when Lennon knocked back Vedran Corluka's cross, Bentley's goalbound 20-yard shot was blocked by Distin.
But Portsmouth doubled their lead in the 67th minute when Crouch grabbed his first goal in front of the Fratton Park fans since joining from Liverpool in the summer.
Traore came raiding again down the left to hit a fearsome drive which Gomes could only knock away - straight to the lurking striker who nodded it into the net to prompt wild celebrations in the stands.
Pavlyuchenko showed a touch of magic at the other end soon afterwards, dribbling past two challenges but then seeing his fierce shot blocked.
Gomes, though, had to race off his line to prevent Crouch grabbing a third Portsmouth goal.
Darren Bent increased their anguish when he fired wildly over the bar with a half-chance, three minutes after his arrival.
Pompey's joy was tarnished when Diarra was sent off for a second yellow card after late-tackling Benoit Assou-Ekotto in the 88th minute.