It was another match to forget for Pompey fans after the ten men of Southend came from behind to win at Fratton Park and inflict a fifth straight defeat on the home side.
Andy Awford's team selection raised a few eyebrows with Jack Whatmough making his debut at centre back in place of Bondz N'Gala and Shaun Cooper playing alongside Johnny Ertl in centre midfield as Simon Ferry faces a scan on his hamstring.
But the new look team got off to a flyer thanks to a thunderbolt from Andy Barcham. The winger cut inside and beat a couple of defenders before hammering the ball into the top corner of the net.
The game descended into a scrap after that but unlike previous matches Pompey were the team winning the battle on the pitch, winning every 50/50 ball and doing a good job of pressuring Southend's players into making mistakes.
Tom Craddock had a golden chance to double the lead late into the second half after evading a challenge in the box and having a clear sight at goal but he blasted the ball wide.
The visitors did have two excellent chances of their own as John White fired wide from close range after the Pompey defence had opened up and Michael Timlin had a free header in the box but couldn't find the target.
But Phil Brown's men were lucky to go in at the break only one goal down as Rob Keirnan turned Jed Wallace's cross against his own crossbar when he quite easily could have scored an own goal.
Pompey started the second half with attacking intent and David Connolly really should have scored when he was found by Dan Potts' through ball but curled the ball wide when he should have found the target.
Despite wasting that chance there seemed to be no danger of Portsmouth losing the game, especially when Cauley Woodrow was sent off in the 65th minute for a clear elbow on Jed Wallace.
However, that seemed to spur Southend on as Pompey became baffled at the prospect of playing against ten men who were fired up and soon found an equaliser when Barry Corr played in Will Atkinson who slotted past the onrushing Trevor Carson.
And Southend soon took the lead when a miscommunication in the defence allowed White to cross for Corr to score and celebrate in pantomime villain fashion having been abused by the crowd for going down easy earlier in the game.
Yet again, Pompey failed to respond to going to behind and kept hopelessly hoofing the ball up to Connolly and Ryan Bird who weren't winning anything up front.
There was one final chance for the hosts as Cooper headed Potts' cross wide from close range and another final whistle was greeted by boos as a stunned Fratton Park crowd had to come to terms with such a shocking defeat.
How on earth does a team go from winning so comfortably and playing well to capitulating in such a dramatic fashion? I'm still confused by it now! What is clear to see, however, is that this latest defeat just highlights the lack of organisation, leadership and character in this team. As soon as the equaliser went in heads dropped and Southend could sense victory despite having ten men.
There's not much more that can be said about the defeat. The effort was certainly there tonight but the nous and the tactical awareness wasn't. Whoever is appointed as the new manager has a serious salvage job to do as this team's confidence is a wreck at the moment.
Pompey Player Ratings
Trevor Carson: 5 - Arguably at fault for both goals but little else to do.
Joe Devera: 4 - Simply not good enough.
Jack Whatmough: 7 - More than decent debut and the result has harsh on him.
Sonny Bradley: 6 - Starting to return to form.
Dan Potts: 6 - Solid in general.
Jed Wallace: 6 - Worked hard.
Shaun Cooper: 6 - Excellent first half but poor in the second.
Johnny Ertl: 5 - Coudln't get hold of the ball.
Andy Barcham: 7 - Exceptional strike and workrate to match.
David Connolly: 6 - Showed some class but should have scored.
Tom Craddock: 6 - Good first touch but wasted a great chance.
Ricky Holmes (Devera 85): N/A - Can't understand why he was dropped.
Jack Maloney (Potts 90): N/A - No time to make an impression on return.
Ryan Bird (Craddock 81): N/A - Long ball up to him didn't work.