A young Pompey side were beaten 2-1 when they travelled to Andover New Street for a Hampshire Cup tie back in 2018.
But the current crop of academy players made no mistake in the latest trip to Foxcotte Park, with a 5-0 victory securing their progress.
Adam Payce bagged a brace, while Jamie Howell, Koby Mottoh and Gabriel Kamavuako also found the target.
And Sam Hudson was delighted with the performance of his side against a team who are unbeaten in the Wessex League this season.
Pompey’s assistant professional development phase coach said: “It’s a good test for our young players to compete against a men’s team – they’re the kind of challenges we want.
“You want to bridge the gap between under-18s and first team football and nights like this, away from home and in front of a crowd, are great, no matter what the result.
"The bravery we showed in and out of possession was really pleasing and we didn’t want to change our style facing a non-league side."
“But we also played fantastically well, got five goals and kept a clean sheet, although if we’re being critical, we probably should have scored a couple more.
“The bravery we showed in and out of possession was really pleasing and we didn’t want to change our style facing a non-league side.
“We have our own identity and a belief in the way we think the game should be played, but you have to earn the right to do that.
“You first need to match the opposition in terms of physicality and putting your bodies on the line, which is exactly what we did.”
Wins over Southampton and Andover mean that Pompey have now made it through to the quarter-finals.
Hudson said: “This is a cup competition and so we said beforehand that we were here to get a positive result.
“It’ll be interesting to see who we get next and then there’s an opportunity to get through to the semi-finals.”
Despite a delayed kick off and the game finishing late and having a long drive home, @PompeyAcademy still made sure the changing room was cleaned last night!
— The Street 💚🖤⚽️ (@AndoverNSfc) December 21, 2022
Thank you!#TouchofClass @Pompey pic.twitter.com/6X0XGJ8Qup