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...
2. Adam Webster - Brighton
The centre-back feature for Brighton in next week's Carabao Cup second-round tie at the Amex. Webster graduated through Pompey's academy and scored five goals in 81 matches before being sold to Ipswich in 2016. He then moved to Bristol City before completing a £20m switch to the Seagulls last summer. Photo: Dan Istitene
3. Kyle Bennett - Bristol Rovers
The winger was a fans' favourite at Fratton Park, helping Paul Cook's side capture the League Two title in 2017. He left for Bristol Rovers in January 2018, but things haven't gone quite as expected so far and may not be included in their 22-man squad for the season. Photo: Mark Kerton
4. Luke Varney - Burton
The striker is still going despite turning 38 later this month. Varney left Cheltenham at the end of last season to return to Burton as player-fitness coach. Netted six times in 31 games during the 2011-12 season at Fratton Park. Photo: Allan Hutchings