After suffering play-off semi-final heartbreak for the past two years, the Blues are looking to go one better this time around and return to the Championship after a 12-year absence.
It’s going to be a long, hectic slog, with the season condensed due to the late start amid the Covid-19 outbreak.
Kenny Jackett’s men will have to overcome several hurdles – and a number of familiar faces will be standing in their way.
There are several former Pompey players plying their trade at rival League One clubs who’re also aiming to have a successful season.
We’ve taken a look at the old-boys the Blues will come up against...
5. Jason Pearce - Charlton Athletic
The ex-Pompey captain remains at The Valley after their relegation from the Championship. The centre-back had two spells with the Blues after coming through the academy, netting twice in 42 matches. Photo: David Rogers
6. John Akinde - Gillingham
The striker failed to score in 11 games during his spell at Fratton Park in 2013. However, Akinde had prolific seasons at Barnet and Lincoln and now gives Gillingham a focal point in attack. Photo: Ashley Allen
7. Oli Hawkins - Ipswich
The big striker was released by Pompey following League One play-off defeat to Oxford. In total he scored 18 goals in 96 appearances during his three years at the club. Hawkins got himself a superb move to Ipswich, though, and will now be aiming for promotion at Portman Road. Photo: Joe Pepler
8. Joe Mason - MK Dons
When the forward arrived from Wolves on transfer deadline day in August 2018, there was a bit of excitement. However, Mason had to settle for a bit-part role at Pompey, making only one league appearance and three in the Checkatrade Trophy. Photo: Pete Norton