Pompey 1 Southend 2
Pompey were left shell-shocked as 10-man Southend came from behind to snatch victory at Fratton Park.
Andy Barcham got the Blues off to a great start with his early strike and victory seemed assured when Cauley Woodrow was given his marching orders after the break.
But that decision seemed to inspire the visitors and a couple of goals in quick succession from Will Atkinson and Barry Corr saw them steal the spoils.
Andy Awford made three changes from the side that lost to Scunthorpe at the weekend.
He handed a debut to 17-year-old centre-back Jack Whatmough and also recalled David Connolly and Shaun Cooper.
Simon Ferry missed out with a hamstring injury, while Ricky Holmes and Bondz N’Gala dropped to the bench.
Kick-off was pushed back 15 minutes because of problems on the A3, but the delay did not seem to affect Pompey and they got off to the best possible start.
It was a super strike from BARCHAM that gave them the lead after just 90 seconds, with the winger cutting inside and hammering home an unstoppable shot from the edge of the area.
The Blues might have doubled their advantage moments later, but Johnny Ertl’s glancing header was cleared off the line by Anthony Straker.
There was not too much to trouble Trevor Carson at the other end, with the keeper comfortably clinging to Ben Coker’s curling free-kick.
It was Pompey looking the more dangerous side going forward and there were half-chances for Jed Wallace and Whatmough as they looked to double their advantage.
But Southend should have been level on 27 minutes when Corr flicked on a corner and John White fired over from just a couple of yards out.
That failed to dampen the Blues’ attacking intent, however, and Wallace drove just wide from distance after being allowed to surge forward unchallenged.
Craddock then had a great chance to get on the scoresheet on 36 minutes, but cleared the crossbar after doing well to skip a challenge and work his way into space.
But the Shrimpers almost levelled just before the break, with Timlin wastefully blazing over from close range.
And there was still time for one more chance deep into stoppage-time when Wallace’s cross was turned against his own bar by Rob Kiernan.
Half Time: Pompey 1 Southend 0
Wallace had a shot blocked and there were a couple of set-pieces nervously cleared as Pompey made a bright start to the second half.
And it looked like the hosts would go further ahead when Connolly raced onto Dan Potts’ pass on 59 minutes.
The striker tried to bend his shout around Daniel Bentley and into the bottom corner, but the ball sailed agonisingly wide of the post.
Southend’s keeper then had his fingertips stung by a Connolly drive from the edge of the box as the Blues tried to make their pressure count.
And they were given a boost on 65 minutes when Woodrow – who had only been on the pitch for four minutes – caught Wallace with his elbow and was shown a straight red card by referee Keith Hill.
That only seemed to fire the visitors up, however, and they soon drew themselves level as Atkinson collected Corr’s pass and slid the ball home.
It almost got worse for Pompey, but Whatmough was able to get the ball clear following an almighty scramble in the box.
But Southend were well on top by now and did forge ahead when White got clear down the right and whipped in a cross that Corr was able to convert.
Awford soon made a couple of changes with Ryan Bird coming on up front and then Ricky Holmes entering the fray soon after.
It was Cooper who had the chance to snatch a late equaliser, though, as he headed over after meeting Potts’ cross.
And that proved to be the final chance for Pompey as they slipped to a fifth successive defeat.
Pompey (4-4-2): Carson; Devera (Holmes 85), Whatmough, Bradley, Potts (Maloney 90+1); Wallace, Ertl (c), Cooper, Barcham; Craddock (Bird 81), Connolly
Goals: Barcham 2
Booked: Whatmough, Craddock
Subs not used: Sullivan, N’Gala, East, Padovani
Southend (4-2-3-1): Bentley; White (c), Kiernan, Prosser, Coker; Clifford (Laird 67), Thompson (Woodrow 61); Atkinson, Timlin (Phillips 90), Straker; Corr
Goals: Atkinson 76, Corr 81
Sent off: Woodrow
Booked: Prosser, Laird
Subs not used: Smith, Payne, Njie, Reid
Referee: Keith Hill
Attendance: 13,427 (773 away fans)