Liam Daish’s youngsters tonight (7.45pm) travel to Farnborough in the Hampshire Senior Cup seeking to maintain their encouraging progress.
A home tie against AFC Portchester next month awaits the winners, with AFC Totton and Eastleigh battling in the other semi-final.
But firstly Pompey must overcome Southern League Premier South side Farnborough, who have a familiar face in their squad.
Ricky Holmes amassed 62 games and netted twice during 18 months on the south coast before departing for Northampton in January 2015.
In his time with the Blues, he also claimed The News/Sports Mail’s Player of the Season in recognition of his displays in the 2013-14 campaign.
He has been sidelined by injury since last month, yet is nearing a first-team return and could be in the frame to face his former club.
Boro also have Frankie Sutherland in their ranks, a former QPR midfielder who made his professional debut while on a one-month loan with Pompey.
That arrived in a substitute cameo against Hartlepool in February 2013, proving to be his first and only outing for the Blues.
And tonight the pair could potentially go head-to-head against what will once again be a youthful Pompey side.
Danny Cowley told The News: ‘We will be fielding an Academy side, the Hampshire Senior Cup has always been an Academy fixture.
‘We had to play some players in the Basingstoke game because we didn’t have enough Academy players, that’s just where we’ve been with players at this football club this season.
‘It’s a brilliant game for them. I can see some benefit in playing some senior players in those games to help the younger ones, but the younger ones have to be ready to step up to these challenges now.
‘The AFC Stoneham game would have been good for them, they would have learnt a lot from that. This will be a tougher test and it will be really good to see how they hope with the demands that a very good Farnborough team will bring.
‘I love those games, it gives you a great opportunity to see young players in more competitive circumstances and how they cope, particularly with the physicality that non-league players bring.’
Pompey have so far beaten Basingstoke and AFC Stoneham to reach the semi-final stage.
Yet this will be the youngsters’ toughest test yet, matched with a Farnborough side who are five points behind leaders Hayes & Yeading with a game in hand.
They compete in the same Southern League division as Gosport, who are presently sixth.
Prices for the Cherrywood Road encounter are £8 for adults, £6 for concessions, £4 for 16-21 year-olds, with under-16s getting in free if accompanied by an adult.
A message from the Editor, Mark Waldron
You can support our local team of expert Pompey writers by subscribing here for all the latest news from Fratton Park for 9p a day, thanks to our 30%-off transfer window deal.