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...
13. Pompey 0 Sunderland 0 (May 16, 2019)
Following a 1-0 defeat at Sunderland in the League One semi-final first leg, it was back to Fratton Park for the decisive match. Certainly a 1-0 deficit could be overturned and the Blues went close when Gareth Evans' header was saved at point-blank range. Kenny Jackett, who had puzzlingly put top scorer Jamal Lowe and Ronan Curtis on the bench, couldn't drag out any sustained attacking threat from the Blues as the match petered out into a goalless draw - and Pompey were eliminated with a whimper. Picture: Habibur Rahman Photo: Habibur Rahman
14. Plymouth 1 Pompey 0 (May 15, 2016)
The 2015-16 League Two Play-Off Semi-final second leg at Plymouth was fascinatingly poised following a controversial 2-2 draw at Fratton Park when Jamille Matt was accused of headbutting Michael Doyle. However, injuries were piling up for the Blues, who already had emergency loan Ryan Allsop in goal. They lost Gareth Evans and Danny Hollands in the first half to serious injury and then suffered the heart-break of a stoppage-time defeat when Peter Hartley headed home. A distraught Paul Cook declined to speak to the local media afterwards, leaving chairman Iain McInnes to take over duties. Picture: Joe Pepler Photo: Joe Pepler
15. AFC Wimbledon 4 Pompey 0 (November 16, 2013)
The new dawn under fan ownership was beginning to turn sour, with Guy Whittingham's side positioned 16th in League Two when they ventured to AFC Wimbledon. The Blues found themselves behind in the first-half, yet collapsed spectacularly late on, conceding three goals in the final 16 minutes in an embarrassing defeat. Ominously, furious chairman Iain McInnes left his seat in the directors' box towards the end and never returned. Whittingham was sacked one game later. Picture: Joe Pepler Photo: Joe Pepler
16. Oxford United 1 Pompey 1 - 4-5 on pens (July 6, 2020)
Pompey's play-off misery continued as they made it eight matches without a win in the format. Their latest heart-break was at Oxford after a 1-1 draw in the League One semi-final second leg made it 2-2 on aggregate. As in the previous season against Sunderland, it was onto penalties to decide the winner - and the outcome was a 5-4 defeat. Loanee Cameron McGeehan missed his penalty in the behind-closed-doors clash at the Kassam Stadium as Oxford progressed to the final. Picture: Robin Jones/Getty Images Photo: Robin Jones