View photos from the Blues' League One loss at Roots Hall
Pompey got off to a disastrous opening as they slumped to a 3-1 defeat at Southend.
The hosts conceded twice inside the first 12 minutes, with Matt Clarke finding his own net and Jason Demetriou adding a second.
Gareth Evans pulled one back for the Blues, only for Nathan Thompson to be dismissed following a late challenge on Ben Coker.
And Demetriou wrapped things up for the Shrimpers late on to dash Pompey's hopes of drawing in the play-off pack.