As Danny Cowley was handed the full-time reins at Fratton Park, a number of his predecessor’s Kenny Jackett senior players sought pastures new.
This saw a mass overhaul of the playing squad, as 11 first-team regulars left for the Championship or League One rivals.
But how did those who departed the Blues in pre-season fare this term, as the curtain fell on the 2021-22 campaign?
Here’s what we found out as some proved the grass is sometimes greener - while others spectacularly didn’t...
1. Charlie Daniels - Colchester United
Daniels was unsurprisingly released at the end of the 2020-21 campaign due to his disastrous spell at Fratton Park. The ex-AFC Bournemouth defender was snapped up by Colchester United where he made 19 appearances before leaving the club in January. In March he started his coaching career at Watford. Picture: Alex Burstow/Getty Images)
Photo: Alex Burstow
2. Callum Johnson - Fleetwood (loan)
Following his red card against Millwall in the EFL Trophy, Johnson was loaned to Fleetwood for the entirety of the season. Since joining the Cod Army, he's been an evergreen by making 35 league appearances as Stephen Crainey's side maintained their League One status. Picture: Richard Heathcote/Getty Images
Photo: Richard Heathcote
3. Jordy Hiwula - Doncaster
Following his release from Pompey, Hiwula joined Doncaster and was relegated at the end of the season. In total he scored once in 25 appearances in all competitions. Picture: Bryn Lennon/Getty Images
Photo: Bryn Lennon
4. James Bolton - Plymouth
Bolton endured an injury-hit campaign with the Pilgrims where he made only 14 appearances and failed to score. His misery was compounded as Plymouth missed out on the play-offs on the final day of the campaign with a 5-0 loss to MK Dons. Picture: Nathan Stirk/Getty Images
Photo: Nathan Stirk