It has been an exile which has brought plenty of heartache and even threats to the Blues’ very existence, yet also plenty of wonderful moments which are still savoured to this very day.
So here’s a list of the 15 most memorable Pompey matches since leaving the Championship – in no particular order...
5. Pompey 3 Exeter 2 (February 18, 2020)
A place at Wembley in the Leasing.com Trophy final was at stake when Pompey hosted Exeter in the semi-final, yet the Blues were heading out 2-1 after Christian Burgess' 89th-minute own goal. That was until Kenny Jackett's men struck twice in stoppage time through John Marquis and Cameron McGeehan to claim a remarkable victory under the Fratton floodlights. Picture: Joe Pepler Photo: Joe Pepler
6. Pompey 6 Cheltenham 1 (May 6, 2017)
Pompey secured the League Two title with a thumping win over Cheltenham having topped the table for the final 32 minutes of the season. Paul Cook's men began the day in third, having already won promotion. They were reliant on top-two Doncaster and Plymouth both failing to win - which is exactly what unfolded. Picture: Joe Pepler Photo: Joe Pepler
7. Peterborough 0 Pompey 1 (March 16, 2024)
Pompey had spent almost six months at the top of League One - yet a 1-0 win at rivals Peterborough was the moment when everyone actually believed. Missing 14 players through illness and injury, the Blues then had to introduce Kusini Yengi for the injured Christian Saydee in the first half. Sure enough, it was the Australian who grabbed the 77th-minute winner to send the travelling 4,019 support wild as the Blues tightened their grip on a promotion spot. Picture: Jason Brown/ProSportsImages Photo: Jason Brown
8. Accrington 1 Pompey 3 (March 8, 2016)
Pompey headed to promotion rivals Accrington requiring a positive result - and found themselves 3-0 up after 43 minutes through Kyle Bennett, Matthew Pearson's own goal and a stunning Michael Doyle volley. Before the match, Blues boss Paul Cook and Accrington manager John Coleman were involved in a huge argument over Romy Boco being named on Stanley's bench, breaking a gentleman's agreement after the Blues let him join them. But Cook had the last laugh. Picture: Joe Pepler Photo: Joe Pepler