Aldershot – the only non-league team to have beaten Pompey as a Football League club.
And on Monday night, Harrogate Town will attempt to match the feat in the same competition which inflicted those life-long scars.
It was as recently as November 2014 when the Shots created history in a competitive match involving Pompey.
Initially the FA Cup first-round tie was staged at Fratton Park, an encounter which saw Andy Awford’s side snatch an equaliser nine minutes from time.
Danny Hollands’ goal spared the Blues' blushes, especially having then to see out the remainder of the match following skipper Paul Robinson’s red card.
With it finishing 2-2, it was back to the Recreation Ground for the replay – and what would prove to be Pompey humiliation.
Chosen for television broadcast, the home audience witnessed a 1-0 defeat for the League Two visitors and a new low in barren times.
Mark Molesley settled matters in Aldershot’s favour on 81 minutes with a scrambling finish, yet Awford’s men had long been struggling to fend off the hosts.
Paul Jones was crowned as The News’ man of the match, such was the extent of his involvement as the visitors produced an abject showing against the Conference side.
Awford heading into the fixture with a first-choice line-up, fielding the likes of Robinson, Nicky Shorey, Craig Westcarr, Hollands, Nigel Atangana, Ryan Taylor and Jed Wallace.
Jack Whatmough is the sole survivor, with Ben Close an unused substitute, although the centre-half was withdrawn for Ben Chorley five minutes before the decisive goal.
In the aftermath of defeat, Alex Wynter, a loanee from Crystal Palace, never played for Pompey again, while Ricky Holmes would feature just twice more, both off the bench.
It would also mark the final appearance of Patrick Agyemang, who was employed as a substitute for the final eight minutes.
As for Andy Scott’s triumphant Aldershot, they included former Pompey keeper Phil Smith and ex-apprentice Joe Oastler, who would later play for Gosport.
Incidentally, their left-back Chris Barker, who went off injured in the first-half, is the brother of ex-Pompey manager Richie.
Days later, Awford signed Mark Fish and Marcus Bean on loan to bolster his shell-shocked squad.
The manager himself continued at the helm until later that season, April 2015, when he departed with the Blues 14th in the table.
Pompey last season avoided another upset to non-league opposition when they comfortably saw off Maidenhead 4-0 at the same stage of the FA Cup.
They will be hoping for similar safe passage at Harrogate Town – and not suffer an Aldershot repeat.