During Pompey’s time in League Two, matches against promotion rivals Plymouth began to take on extra significance.
And now a rivalry is starting to develop with Sunderland in the third tier, as both sides continue to battle for a return to the Championship.
There were five closely-fought meetings between the cross-country giants last term, with both sides enjoy joy and despair.
It was the men from the south coast who triumphed at Wembley following a penalty shoot-out to lift the EFL Trophy.
But the Black Cats got their revenge by edging a two-legged play-off encounter, even if heartache followed against Charlton in the final.
Now the latest chapter of an epic tale is about to take place on Wearside, with television cameras on hand to beam the action live around the world.
Sunderland were notoriously hard to beat last season, suffering a divisional low of just six league losses.
And it was ultimately their failure to convert draws into wins that cost them promotion, with an incredible 19 games finishing all square.
So supporters might be worried that their first two games of the current campaign – against Oxford and Ipswich – ended 1-1.
They did break their duck earlier in the week, however, with a 3-1 success at Accrington in the Carabao Cup.
James Bolton has returned to full fitness for Pompey, but Oli Hawkins is out of action with a slight foot injury.
The striker joins Bryn Morris (groin), Jack Whatmough (knee) and Ryan Williams (quad) on the sidelines.
Glenn Loovens, Ethan Robson and Duncan Watmore are all on Sunderland’s injured list, but Denver Hume and Dylan McGeouch are back in contention.
HEAD TO HEAD
Pompey: 34 wins
Sunderland: 38 wins
Pompey: 9 wins
Sunderland: 27 wins
Pompey fans will be able to buy tickets at the Stadium of Light on the day of the game. Click here for more information.
Referee: Michael Salisbury
Assistants: Joe Simpson and Gareth Mellor
Fourth Official: Paul Marsden
The game has been selected for live television coverage, so there will be no video on iFollow for overseas subscribers.
Viewers in the UK can watch the game live on Sky Sports Football, while overseas supporters should check their local listings.
ALSO IN LEAGUE ONE
All matches kick-off at 3pm
AFC Wimbledon v Accrington
Blackpool v Oxford
Burton v Rotherham
Coventry v Bristol Rovers
Doncaster v Fleetwood
Lincoln v Southend
Peterborough v Ipswich
Shrewsbury v Rochdale
Tranmere v Bolton
Wycombe v MK Dons