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...
9. Dan Butler - Peterborough
Another former Blues youngster. The Isle of Wight left-back was released by Paul Cook after he took charge in 2015. Butler dropped to non-league to join Torquay then moved to Newport before completing a switch to Peterborough last summer. He scored in the Posh's 2-0 win over the Blues at London Road last term and will firmly be aiming for promotion. Photo: Simon Davies
10. Nathan Thompson - Peterborough
The right-back was popular on the south coast, with his tough tackling and penchant to win cheap free-kicks going down a storm with fans. Left in the hope of playing Championship football but had to settle for Peterborough last summer. Thompson's recently been appointed vice-captain at London Road. Photo: Simon Davies
11. Brett Pitman - Swindon
Pompey will be hoping the striker doesn't come back to haunt them after his release earlier this summer. Pitman left under a cloud after being sent to train with AFC Bournemouth at the start of the year then not returning for training ahead of the play-offs. Netted 42 goals in 99 games for the Blues and still knows where the net is. Photo: Joe Pepler
12. Dion Donohue - Swindon
The Welshman is still to sign a contract at the County Ground, although Richie Wellens has said it's likely to happen. Donohue's trained with Swindon all summer, after a short spell at the club last season following his sacking from Mansfield. Pompey will have to be wary of his dangerous set-pieces and crosses if he does come up against them. Photo: Joe Pepler