It's five defeats from eight in 2018 for Pompey after another below-par showing at Southend.
Pompey - unchanged from the midweek defeat to Blackburn - started well but were behind on six minutes when the unfortunate Matt Clarke guided the ball past Luke McGee when he tried to stop Shayon Harrison in his tracks.
The large away following soon got the feeling it was to be another of those days when Jason Demetriou finished well to make it 2-0 with only 12 minutes gone.
Gareth Evans sparked hopes of a comeback when he forced the ball home from close range nine minutes before the break after Brett Pitman had put Jamal Lowe's cross back into the goalmouth. Evans was hurt in the process of scoring and had to limp off.
Pitman, Lowe and Conor Chaplin gave the Southend defence some uncomfortable moments but there was a big setback on 64 minutes when Nathan Thompson was shown a straight red card for a late tackle. It looked rather harsh.
Pitman followed Evans into the treatment room as he hobbled off, and to rub salt into Pompey's wounds Southend clinched the points six minutes from the end with a simple goal, his second of the afternoon.
Pompey are on the road again on Tuesday when they go to Fleetwood, who will be playing for a new manager after Uwe Rosler was sacked. Pompey have lost seven out of 10 away from home and need to improve that record.
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