Pompey are tantalisingly close to progressing in the Premier League Cup following victory at Wolves under-23s.
The Blues’ reserves added the hosts to their recent Championship scalps in a competition which saw them last month inflict a 4-0 win over Norwich.
Tonight the scoreline was 4-2, lifting the visitors above Everton at the top of Group D.
With two teams from the four-strong group qualifying for the next round, it puts Pompey firmly in pole position.
Victory was assured through a strong team performance from an experienced starting XI, containing many first-team players.
Kal Naismith was among the scorers at New Bucks Head, while the ever-lively Conor Chaplin had a hand in three of the goals.
There were also outings for Drew Talbot, Liam O’Brien, Tom Davies and Jack Whatmough, with Nicke Kabamba netting his second goal for the club.
For under-18s coach Mikey Harris, there was also pride at seeing first-year Academy midfielder Dan Smith climb off the bench to net the fourth goal of the game.
Earlier, Wolves’ Connor Johnson turned Brandon Haunstrup’s cross past his own keeper.
And for Harris, the result was fully deserved.
He said: ‘We had some very, very good chances throughout the game, as did Wolves, and it must have been entertaining to the neutrals.
‘At half-time we talked about the importance of scoring the next goal having been 2-1 up – and we managed to get that through the own goal.
‘In the end we needed that because they came back to 3-2 before Dan Smith made sure when he came off the bench.
‘I’m delighted for him, it was a nice little moment for somebody making their reserve debut.
‘Overall, though, it was a pleasing night and a game we deserved to win against a very good side.’
Wolves broke the deadlock on 10 minutes through Connor Ronan’s 25-yard free-kick.
Within minutes, Kabamba headed home Chaplin’s cross, while Naismith handed Pompey the lead before half-time.
Johnson’s own goal made it 3-1 before Donovan Wilson reduced the deficit. It was left for substitute Smith to secure victory minutes from time.
POMPEY: O’Brien, Talbot, Whatmough, Davies, Haunstrup, Oxlade-Chamberlain (88 mins McDowell), Widdrington, Bedford (80 mins Smith), Naismith, Chaplin, Kabamba. Sub Not Used: Hall.