Pompey Reserves suffered more Central League Cup disappointment after losing 2-0 to Bristol City at Gosport’s Privett Park.
Brandon Haunstrup, Milan Lalkovic and Danny Rose were all given a chance to impress in the group stage contest.
But goals from Kel Akpobire and Connor Lemonheigh-Evans ensured the Blues endured their second defeat in this season’s competition.
The visitors won an early free-kick in a dangerous position that Lemonheigh-Evans fired narrowly past the post.
A neat move for the visitors then presented a chance for Jake Andrews, who fired high and wide of Alex Bass’ goal.
Christian Oxlade-Chamberlain embarked on a mazy run that took him past three players at the other end, but after cutting inside, his cross came to nothing.
That was a familiar tale throughout the first half, with plenty of promising moves breaking down in the final third.
Pompey finally tested Max O’Leary when Matt Mayes’ shot deflected off Tin Plavotic, although the Robins keeper was not overly troubled.
And a Theo Widdrington effort was then heading for the target, only to hit an opposition defender and fly behind.
But it was the visitors who forged ahead on 42 minutes, as Bass kept out Aden Baldwin’s header, only for Akpobire to convert the loose ball.
Half Time: Pompey 0 Bristol City 1
Bristol City doubled their advantage just after the restart when Lemonheigh-Evans was upended in the box by trialist Ceykan Karagozlu.
Referee Barrie Small pointed to the spot and Lemonheigh-Evans dusted himself down to convert the penalty.
With a firm hold on the contest, the Robins appeared comfortable as Pompey laboured away without reward.
But the hosts suddenly started to threaten as the second half progressed and Theo Widdrington’s free-kick had to be tipped over by O’Leary.
They soon went even closer to scoring, with Jez Bedford firing against the post after seizing on Lalkovic’s teasing delivery.
Matt Casey then rose to head narrowly wide, while Lalkovic jinked into the area and saw his shot saved by the legs of O’Leary.
Pompey thought they had reduced their deficit when Bradley Lethbridge’s low cross was stabbed home by Widdrington, only for a linesman’s flag to dampen spirits.
And the lively Lalkovic then had another attempt blocked, as the Blues failed to find a way through the Bristol City defence.
Pompey: Bass; Oxlade-Chamberlain, Casey, Dandy (Chandler 74), Haunstrup; Rose (c), Widdrington; Karagozlu (Smith 63), Bedford (Brooks 74), Lalkovic; Mayes (Lethbridge 63)
Sub not used: Collins
Bristol City: O’Leary; Parsons (Harper 76), Baldwin (c), Plavotic (Smith 63), Nurse; Andrews, Morton, Richards, Holden; Lemonheigh-Evans, Akpobire
Subs not used: Sainsbury, Ali
Referee: Barrie Small