Two first-half goals saw Pompey fall to pre-season defeat at Sutton United today.
Efforts from former Blues triallist Roarie Deacon and Bedsente Gomis earned the National League South champions a 2-1 success.
Youngster Christian Oxlade-Chamberlain pulled a goal back with nine minutes left with his first effort at senior level.
Paul Cook’s side were second best for the first 45 minutes and periods of the second half on the artificial 4G surface at Gander Green Lane.
But they finished much the stronger side with a more powerful side on the pitch after a swathe of changes.
Pompey were slow to start and fell behind after eight minutes.
It was Deacon who did the damage as he reached Dan Spence’s cross and cut across the box before firing past the exposed Alex Bass.
Some smart play from Brandon Haunstrup and Curtis Main created a chance for Chaplin after 17 minutes, but he fired at Ross Worner.
Dan Wishart left Chris Sessegnon for dead eight minutes later but smashed his shot at Bass instead of cutting the ball back across the face of goal.
Sutton should have had a second after 32 minutes when Bedsente Gomis headed off the bar from Roarie Deacon’s cross.
Gomis got his goal moments later, though, as he powerfully headed past Bass.
Sutton should have had a third two minutes after the restart but Craig Eastmond blasted over Deacon’s cross with the goal at his mercy.
Curtis Main fashioned a chance of his own after 53 minutes when he fired just over from 35 yards.
And he was the width of the bar from pulling a goal back five minutes later as his delicate lob came back off the woodwork.
Youngster Theo Widdrington was close to his first senior goal after a rash of Pompey subs, but saw his effort blocked in a melee.
Then both Gary Roberts and Carl Baker had efforts saved as the Blues took control with a more powerful side on the pitch.
Pompey’s pressure saw them pull a goal back with nine minutes left, as Hunt took a quick free-kick and Baker crossed for Oxlade-Chamberlain to slide the ball home.
Cook’s side continued to push through the game’s dying embers but there was no late leveller.
Pompey now travel to Salisbury on Tuesday night (7pm).