Last term was deemed by many as a transitional one for the Blues, as Danny Cowley put his stamp on the team he inherited.
However, that wasn’t the case for a swathe of familiar ex-Fratton Park faces, who will be playing in a higher division come August following successful campaigns with their new clubs.
But who are they? And where did they find success?
Here’s all the former players to wear royal blue who won promotion last season.
9. Andy Cannon - Stockport
Cannon raised eyebrows when he joined the National League side from Championship Hull on loan in March. However, his objective of reaching League Two proved successful as Dave Challinor's side lifted the title. In total, Cannon made nine appearances for the League Two new boys. Picture: Alex Livesey/Getty Images Photo: Alex Livesey
10. OXFORD, ENGLAND - OCTOBER 08: Josh Flint of Portsmouth during the Leasing.com Trophy match between Oxford United and Portsmouth at Kassam Stadium on October 08, 2019 in Oxford, England. (Photo by Catherine Ivill/Getty Images)
The Pompey academy graduate won promotion to the Eredivise with FC Volendam last term. The newly-adopted centre-back played 15 league games and scored once. Picture: Catherine Ivill/Getty Images Photo: Catherine Ivill