Pompey Reserves opened their Central League Cup account with a 5-2 defeat to Southend United.
The Blues’ side was made up entirely of academy players due to the first team’s League One clash at Coventry tonight.
Mark Kelly’s troops delivered a plucky performance but the Shrimpers’ extra experience told in the end at the club’s Roko training base.
The visitors made the better start and almost took the lead after two minutes.
A corner from the right was met by Miles Nelson but his header hit the post.
Four minutes later Renei Batlokwa stole the ball from Ethan Robb in a dangerous area. However, the forward’s shot was saved by the legs of Pompey keeper Lewis Boughton.
Southend continued to put the Blues on the back foot and broke the deadlock in the 29th minute through Norman Wabo’s 20-yard right-footed shot which curled into Boughton’s left-hand post.
Kelly’s troops responded superbly, though, and equalised through Leon Maloney’s brilliance.
The striker skipped away from Nelson and Tom Clifford before being brought down inside the box.
Maloney stepped up and tucked his penalty beyond visiting keeper Harry Seadan in the 32nd minute.
The Isle of Wight talent should have been awarded a second spot-kick a minute later when he was hacked down by Nelson but the referee waved play on.
Southend managed go into the interval ahead courtesy of Matt Rush, who steered a close-range header home on 44 minutes.
The Blues came out fighting in the second half and should have been level just seconds after the restart.
Alfie Stanley found himself one-on-one with Seadan but crashed his shot against the crossbar.
Two minutes later Josh Flint’s corner found Haji Mnoga but the defender couldn’t keep his effort down.
Despite their bright start, Pompey conceded in the 58th minute when Rush was left in space and slotted home for his second of the game.
And the Shrimpers forward rounded off his hat-trick two minutes later when he was left unmarked from a cross at the back post and bundled the ball into the back of the net.
Kelly’s side reduced the arrears through a cool finish from Stanley in the 80th minute.
But they were unable to close the deficit further and Charlie Kelman added a fifth for Southend with the final kick of the game.