Former Tottenham striker Jermain Defoe scored against his old club on Sunday to help earn Portsmouth a 2-0 Premier League victory at Fratton Park and keep Spurs bottom of the table.
Defoe, who left Tottenham in January after failing to hold a regular starting place, put Portsmouth ahead from the penalty spot in the first half after a handball by Jermaine Jenas.
Peter Crouch, who was once on Tottenham's books without making a first-team appearance, headed the second after the break when Spurs keeper Heurelho Gomes was at fault.
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In the day's other action Manchester City, the richest club in the country after their takeover by an Abu Dhabi investment group, stumbled to a 2-1 defeat at Wigan Athletic, missing the chance to go into the top four.
Tottenham are fast emerging as rivals to Newcastle United as relegation contenders and they looked desperately short of firepower, passion and confidence at Portsmouth.
Playing with just Russian striker Roman Pavlyuchenko up front they created next to nothing and not even the late sending off of Portsmouth's Lassana Diarra for a rash challenge could spark a revival from the visitors.
Defoe did not celebrate when he beat Gomes from the spot with a penalty after 34 minutes, following a needless handball by Jenas. When he was substituted near the end he was even applauded by the visiting fans who voiced their disapproval towards manager Juande Ramos.
Spurs had a penalty appeal turned down when substitute Aaron Lennon's cross appeared to be blocked by the hand of a defender. Crouch made sure of the points after 68 minutes when he nodded in his first goal since joining from Liverpool.
Defeat kept Tottenham bottom of the table with just two draws to show from their six league games so far.
Portsmouth, who lost 6-0 at Manchester City last week and 4-0 at home to Chelsea in the League Cup in midweek, eased into mid-table with nine points.
Wigan's Amr Zaki scored his fourth league goal of the season to earn Wigan the points, slotting in a penalty after City's Vincent Kompany had cancelled out Antonio Valencia's opener.