Liverpool's miserable season hit a new low as Javier Mascherano was sent off in the defeat at Fratton Park.
Algerian defender Nadir Belhadj rifled in an unstoppable volley in the first half before Frederic Piquionne capped a good afternoon for Portsmouth manager Avram Grant late on.
Rafael Benitez's side, who are already out of the European Champions League, have won just four of their last 17 matches in all competitions and face a desperate fight to salvage a place in the English Premier League's top four.
The Reds, who are five points adrift of fourth place ahead of Saturday's later games, fell behind in the 33rd minute when Belhadj lashed a ferocious shot past Jose Reina from a tight angle for his first goal of the season.
That strike was the 500th in the Premier League this season and Liverpool defender Daniel Agger should have added to that tally, but wasted his side's best chance when he headed over from close range.
A dismal day for Liverpool got even worse when Argentine midfielder Mascherano was dismissed by referee Lee Mason for a lunge on Tal Ben Haim just before half time.
French striker Piquionne piled on the misery for Liverpool boss Benitez, who is certain to face more heavy criticism after this defeat, when he finished off a Kevin-Prince Boateng move in the 82nd minute with another angled volley.
Portsmouth, celebrating their second win under Grant, move level on points with second bottom West Ham, but remain behind the Hammers on goals scored.
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