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...
13. Kal Naismith - Wigan
The Scot is one of few senior players who remains at Wigan after they enterted administration and been forced to sell assets like Jamal Lowe. Naismith was Pompey's talisman during the business end of the League Two title triumph in 2017 and also finished last term in top form for the Latics. Photo: .
14. Gary Roberts - Wigan
After being deemed surplus to requirements by Kenny Jackett three years ago, the cultured midfielder is still playing aged 36 and spent the past two years in the Championship for Wigan. The Liverpudlian, who scored 20 goals in 80 appearances and helped Pompey to the League Two title in 2017, recently penned a new short-term deal at the DW Stadium. Photo: Joe Pepler
15. Viv Solomon-Otabor - Wigan
The winger's time at Fratton Park will always be remembered for running offside against Peterborough in April 2019, which ended Pompey's automatic promotion hopes. Still, the winger is a talented player and joined Wigan on a short-term deal after returning from Bulgaria having played for CSKA Sofia. Photo: Joe Pepler