Southend came from behind to win at Fratton Park and extend Portsmouth’s winless league run to eight games.
Pompey started brightly and took the lead when Andy Webster rose highest to head in Craig Westcarr’s free-kick.
The lead did not last long and David Worrall headed across goal for Ryan Leonard to cushion in the equaliser.
Joe Pigott picked up Barry Corr’s knock-down to fire a deflected winner before both Corr and Pompey’s Paul McCallum saw red in the closing stages.
Corr picked up a second yellow card for kicking the ball away before McCallum received a straight red for violent conduct in the dying seconds.
Portsmouth manager Andy Awford told BBC Radio Solent:
“Another frustrating afternoon; there’s not a lot in the game so it’s fine lines. We haven’t won in an awful long time now. It’s a tough time for everyone at the football club and we have to start turning half decent performances.
“It’s probably not as good as last week, it’s very fine lines and we have to start turning those performances into results and unfortunately today we couldn’t do that.
“I understand the pressures of the job and that goes with being a first-team manager.
“I take full responsibility for the team out there, I pick the players and I take full responsibility for that. There’s no ducking out, I will always come out, talk to you guys and say how it is.”
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