Jermain Defoe returned to haunt Tottenham manager Juande Ramos as the Portsmouth striker set up a 2-0 victory that kept his former club rooted to the bottom of the Premier League on Sunday.
Defoe was allowed to leave White Hart Lane last season after failing to impress Ramos but the England star got his revenge at Fratton Park.
He opened the scoring with a first-half penalty after Jermaine Jenas had handled the ball and played a key role in Peter Crouch's second-half header.
Portsmouth had Lassana Diarra sent off in the closing moments but Spurs couldn't avoid a fourth defeat in six league matches.
Ramos's side have made their worst start for 53 years and increasingly resemble a team in total disarray.
The pre-season departures of Dimitar Berbatov and Robbie Keane have left them bereft of any attacking threat. Ramos appears uncertain how to get the best out of his new signings.
While it is too early to talk of a relegation fight, Spurs' lofty ambition to break into the Champions League places has already been reduced to a pipe-dream.
Portsmouth had conceded 10 goals in their last two games so manager Harry Redknapp was relieved to welcome back former Tottenham centre-half Sol Campbell and French midfielder Diarra.
Defoe was playing against his former club for the first time and the Portsmouth forward had the ball in Tottenham's net in the third minute, but his clinical strike was ruled offside.
Ramos's side were set-up in damage-limitation mode with five players in the midfield but the side cracked in the 33rd minute.
Glen Little whipped in a free-kick from the right and Jenas rashly stuck out his arm to control the ball.
Referee Mike Dean pointed to the spot and Defoe sent his penalty past Gomes. He made a point of keeping his celebration to a minimum as a mark of respect to his former supporters packed behind Gomes's goal.
Portsmouth went further ahead in the 68th minute.
Defoe turned Dawson on the edge of the area and picked out Armand Traore wide on the left. The on-loan Arsenal youngster drove in a low shot that Gomes could only parried towards Crouch, who rose to head into the empty net from close-range.
The sense of crisis enveloping Spurs deepened when Ramos's decision to send on Bent in place of Roman Pavlyuchenko was greeted by chants of "you don't know what you're doing" by Tottenham's fans.