Although five of whom returned to their parent clubs after their stays came to an end, nine others ventured for new beginnings elsewhere.
Academy stars Alfie Bridgman and Toby Steward have recently joined Bognor on a temporary basis, while all the other names would make permanent moves away from PO4.
But how have the 14 players who departed Fratton Park this summer got on since their time with the Blues came to a close?
We’ve taken a look at those names and have started at their new homes.
9. Tyler Walker
After his move failed to work out at Pompey, the striker returned to Coventry but has been a regular in Mark Robbins’ pre-season squads. The 25-year-old travelled to Spain with the Sky Blues and scored a double against Nottingham Forest, while also missing a penalty against the Blues at Fratton Park in their final summer test. Walker featured as a second-half substitute against Sunderland in City’s season-opener in the Championship. Photo: Nigel Keene
10. Shaun Williams
After being released by Pompey, the 35-year-old reunited with former boss Neil Harris at Gillingham and featured in all five of the Gills’ pre-season friendlies. The former Millwall man appeared against the Blues as Danny Cowley’s men won 2-1 at Priestfield Stadium. Williams played the full 90 minutes as his side lost 2-0 against AFC Wimbledon on the opening day in league Two. Photo: Jason Brown
11. Marcus Harness
The winger joined rivals Ipswich for an undisclosed fee two weeks ahead of the new League One campaign. Following his switch, the 26-year-old made just one pre-season outing, where he came on as a late substitute against Southend. Harness made his Tractor Boys debut against Bolton on Saturday but failed to make an impact and was substituted on the hour-mark. Photo: Jason Brown
12. Alex Bass
The keeper was the longest-serving player at Fratton Park before he joined Sunderland for an undisclosed fee last week. Despite spending all of pre-season with Pompey, Bass appeared on the bench for the Black Cats in their season opener against Coventry on Sunday. Photo: Graham Hunt