Charly Musonda’s last-ditch free-kick saw Pompey’s Checkatrade Trophy run come to a close.
Musonda’s superb effort won the game for Chelsea under-21s as they ran out 2-1 winners at Fratton Park.
There was late drama with Brett Pitman levelling in stoppage-time before Musonda won it in front of a crowd of 3,113 in the much-maligned competition.
The Belgian under-21 international opened the scoring in the 58th minute after Kenny Jackett’s side had a stack of chances they failed to make count,
Pompey had much the better of it for long periods but were undone by the swiftness of the visitors’ counter-attack, in a match which proved a useful work out for a strong Pompey side who have not played since New Year’s Day.
The first half was a tale of Pompey pressure and chances without making a breakthrough. Connor Ronan, on his Blues bow, had an early 20-yarder saved by Marcin Bulka.
The visitors replied in the 17th minute as Callum Hudson-Odoi got the wrong side of Nathan Thompson but Luke McGee stood up to his finish from a tight angle.
Oli Hawkins had two quickfire chances in the 33rd minute saved by Bulka, either side of Lowe’s effort being blocked by Kyle Scott.
Christian Burgess and Ronan also had efforts fly over as the Pompey pressure continued before the break.
Jackett’s men were hurt by not taking one of their many chances as Musonda opened the scoring 13 minutes after the restart.
The Belgian talent stroked home his 10-yard finish from Scott’s cutback as Pompey were opened up on the counter.
Strong appeals for a handball in the box against Ethan Ampadu were not given in the 67th minute as the pattern returned to pressure from the home side.
Then McGee made a great reaction stop to keep out Scott’s first-time effort from Harvey St Clair’s ball in.
Pompey had 10 men on the pitch late on when Ben Close limped off but there was Pitman to level from close range in stoppage-time from Matty Kennedy’s cross.
But there was one late twist as Burgess took down Hudson-Odoi on the edge of the box and Musonda applied the finish.