A Pompey XI conceded two late goals to lose to Chelsea U23s in a pre-season friendly at the Londoners’ Cobham training base.
Substitute Malik Mothersille capitalised on a couple of moments of defensive uncertainty to settle the contest.
It had been a fairly close contest up until that point, with Michael Jacobs and Reeco Hackett-Fairchild going closest for the Blues.
There was a first outing for Gavin Bazunu, who had picked up a quad injury shortly after his loan arrival from Manchester City.
Jacobs is also fully fit from his knee problem and was named skipper following a cameo appearance at Luton on Saturday.
Danny Cowley rested all those who started that Kenilworth Road contest, with Callum Johnson, Haji Mnoga, Ellis Harrison and Hackett-Fairchild joining a mixture of trialists.
Both sides looked comfortable in possession once the action started and looked to pass the ball around.
But it was the home side that were first to threaten and Bazunu got down to his left to make a key save.
Jacobs was at the heart of all the Blues’ threatening attacks and there was an opportunity to break the deadlock when he was felled on the edge of the box.
One of the trialists sent the resulting free-kick into the wall, however, and when the ball was recycled, another narrowly cleared the crossbar.
Jacobs had a chance of his own before the break and hooked his opportunistic effort onto the roof of the net.
Half Time: Chelsea U23 0 Pompey 0
It was Pompey who made the stronger start to the second period and won a series of corners that the hosts had to deal with.
And Hackett-Fairchild almost broke the deadlock by chesting down a cross and drawing a smart stop from Chelsea’s substitute stopper.
There was also an opportunity for Harrison just before the hour mark, but the striker could only scuff an attempted volley.
Both sides made changes as the half progressed, including – confusingly – some of the trialists who had gone off coming back onto the pitch.
Bazunu also made way for a trialist stopper, who was quickly called into action to push a shot around the post.
There were threats at both ends of the pitch as the seconds ticked down, but it was the Londoners who finished with a flourish.
Cowley will be disappointed with the defending, however, as Mothersille capitalised on an under-hit back-pass to slot home the opener on 78 minutes.
And when Mnoga was robbed in possession a few moments later, the ball was squared for the same player to tap home a second.
Pompey (4-1-4-1): Bazunu (Trialist G 63); Johnson, Mnoga, Trialist A (Trialist H 66), Trialist B; Trialist C (Trialist A 77); Hackett-Farchild, Trialist D, Trialist E (Trialist F 46), Jacobs (c) (Trialist E 63); Harrison (Trialist I 77)