Pompey Academy conceded in stoppage-time as they fell to a 3-2 defeat at Southend in Merit League One.
The visitors had been rewarded for a bright start when an effort from Bradley Lethbridge (pictured) went in off the post following good work by Dan Smith.
But the Essex side hit back before the break, as Terrell Egbri stole the ball from Leon Pitman and tapped into an empty net.
They then forged ahead early in the second half, thanks to a thumping Taylor Curran header to convert Jon Benton’s cross.
Smith came close to a leveller with a free-kick that crashed into the post, but the ball was sent back into the box for Stan Bridgman to nod home.
The Blues set about trying to find a winner, only to be left with nothing when Matt Rush completed a quick counter-attack.
Professional development phase coach Liam Daish said: “We certainly did enough to deserve something from the game, but didn’t capitalise on our dominance in possession.
“Our start was impressive and we scored a good goal to take the lead, only to then concede two poor ones either side of the break.
"It was the perfect time to score for them and the worst for us. It didn’t really leave us with enough time to regroup and respond."
“We applied plenty of pressure after that and managed to get back on level terms before trying to find a winner.
“It wasn’t just a case of shutting up shop to settle for a point and Southend had to make a couple of goal-line clearances.
“But they won it late on with a goal that probably should have been dealt with at source. We paid the price for not doing that.
“It was the perfect time to score for them and the worst for us. It didn’t really leave us with enough time to regroup and respond.
“There were still some encouraging performances from our side, though, and we played the better football against a physical and hard-working team.”
Pompey: Pitman; Johnston (Bridgman 60), Casey, Dandy, Hancott; Flint, Read, Maloney, Whiting (Stanley 74); Smith, Lethbridge
There was better news for Pompey’s under-16 side, who triumphed 3-2 over the same opponents.