The Blues’ Academy side faced the Royal Artillery in a historic nod towards one of the forerunners of the club’s April 5, 1898 inception.
Pompey wore this season’s third strip for the commemorative fixture, with the salmon pink kit reflecting the colours of the club’s opening decade of existence.
The kids found themselves trailing 2-0 to the Royal Artillery after 53 minutes, following a double from Gunner Harry Beckley at Privett Park.
However, just as the previous Wednesday when they recovered from three goals to beat Gosport in the Hampshire Senior Cup, they staged an impressive fightback.
It was led by Sam Folarin, who was introduced at half-time and scored twice, including the winner from the penalty spot eight minutes from time.
Spencer Spurway also netted in another remarkable comeback from Sam Hudson’s kids as it finished 3-2 at the home of Gosport.
Pompey’s team consisted of eight of the side which started the Hampshire Senior Cup second round victory over Gosport.
However, a notable absentee was Koby Mottoh, who netted twice in the eventful fixture plus the winning penalty in the shoot-out.
Instead the winger had been called up for first-team duty to provide cover for injured duo Anthony Scully and Gavin Whyte in the forthcoming trip to Derby.
The Gunners opened the scoring on eight minutes when Beckley drove in a shot from inside the box which found the far bottom corner of the net.
It was a well-placed finish from the striker, who turned to embrace the congratulations of his team-mates in recognition of their early 1-0 lead.
Pompey came agonisingly close to levelling on 22 minutes when Mitch Aston’s left-wing corner was headed against the bar by Cody Howard.
Then the visitors’ keeper Chandler Harris produced a stunning save to somehow tip over Luke Staight’s viciously-curling right-footed shot delivered from just outside the box.
However, the Royal Artillery doubled their advantage on 30 minutes from an excellent cross from the right by Ryan Lewis.
Bastian Smith couldn’t quite claim it, deflecting the delivery away, but it was picked up by Beckley who grabbed his second with a right-footed finish into the far corner.
With half-time approaching, Howard’s header from another left-wing corner was cleared off the line by Luke Holden, positioned by the right-hand post.
Pompey made a double substitution at the break with Folarin and Christian Ayres introduced for Dan Murray and Kevin Bosaka.
It was Folarin who gave them a lifeline on 53 minutes when he capitalised on Frank Maloney’s weak backpass.
The substitute intercepted before calmly rounding the keeper and firing a left-footed finish into the net, past a defender on the line, to make it 2-1.
On the hour mark, skipper Jack Fox drove forward with the ball before unleashing a right-footed shot from long-range which drew a solid save from the keeper.
It was 2-2 on 77 minutes through a stunning 25-yard strike from Spurway, having been pushed into the centre of midfield.
He received a ball from the left, took a touch and drove in a right-footed shot perfectly placed into the far bottom corner to level.
Then, on 82 minutes, Tayo Singerr earned a penalty after being brought down while charging into the penalty area, with Folarin netting the spot-kick to make it 3-2.
And that’s how it stayed as the Blues’ youngsters savoured the big occasion.
Pompey: Smith (63 mins Glover), Howard, Spurway, Fox (63 mins Quarm), Bosaka (46 mins Ayres), Triallist (63 mins Singerr), Murray (46 mins Folarin), Aston (63 mins Buckland), Staight, Keteku (63 mins Mullins), May (63 mins Whitelock).