It has been quite a journey, with two league titles and the Checkatrade Trophy to show for an exile that began in 2012 with relegation under Michael Appleton.
There have also been plenty of gutting lows during the long battle to return to the Championship – and not just restricted to awful owners and High Court battles.
So here’s a list of the 20 worst Pompey matches since leaving the Championship – in no particular order...
9. Northampton 4 Pompey 1 (March 6, 2021)
In one of the worst performances of the Kenny Jackett era, the Blues found themselves 4-0 down after 43 minutes in the behind-closed-doors trip to struggling Northampton. It was an absolutely shocking first-half showing from a Blues side occupying fifth heading into the fixture, later grabbing a consolation through substitute Ellis Harrison's penalty. Picture: Pete Norton/Getty Images. Photo: Pete Norton
10. Aldershot 1 Pompey 0 (November 19, 2014)
Pompey suffered defeat to a non-league side in a cup competition for the first time in their Football League history. The Blues had drawn 2-2 to Aldershot at Fratton Park in the FA Cup first round fixture, allowing the non-leaguers to take Andy Awford's men to their place. The televised clash saw Mark Molesley grab a 81st-minute winner to mark a truly embarrassing result for the Blues. Picture: Joe Pepler Photo: Joe Pepler
11. Pompey 2 Peterborough 3 (April 30, 2019)
In the penultimate match of the 2018-19 season, third-placed Pompey had to beat Peterborough at Fratton Park to maintain their automatic promotion challenge. With the game poised at 2-2, Brett Pitman broke down the right-hand channel and, with just the keeper to beat, unselfishly squared for Viv Solomon-Otabor to slot into an empty net to give the Blues the lead. However, it was rightly ruled out for offside - and minutes later Ivan Toney grabbed the winner for Peterborough. Picture: Robin Jones. Photo: Robin Jones/Digital South
12. Pompey 0 Southampton 4 (September 24, 2019)
In the first meeting between the south-coast neighbours for more than seven years, it was the Premier League visitors who ran out comfortable winners at Fratton Park. Danny Ings' first-half double put Southampton well in control in the Carabao Cup fixture, before two goals in the final 13 minutes made it a miserable 4-0 defeat for Kenny Jackett's men. Picture: Habibur Rahman Photo: Habibur Rahman