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...
9. Craig MacGillivray - Charlton
MacGillivray became the latest winner of The News/Sports Mail Player of the Season to depart immediately after claiming the award. The keeper moved to Charlton for free, but hasn't endured an up and down season. The Addicks parted ways with Nigel Adkins and Johnnie Jackson in the dugout as they finished 13th. Picture: Justin Setterfield/Getty Images) Photo: Justin Setterfield
10. Ben Close - Doncaster
Alongside Hiwula, fans' favourite Close joined Doncaster, too. Relegation to League Two was the unfortunate outcome for the Pompey academy graduate who suffered an injury-hit campaign. Picture Howard Roe/AHPIX LTD, Football, Sky Bet League One, Photo: HOWARD ROE, Howard Roe/AHPIX LTD
11. Andy Cannon - Stockport (on loan from Hull)
Eyebrows were raised when Cannon joined Championship Hull in the summer. The 26-year-old then scored on debut for the Tigers in a 4-1 win over Preston, but was then blighted by injuries and appearances became few and far between. Eyes-widened further when he dropped three division to join Stockport on loan in the National League. Since then he's made seven appearances as Dave Challinor's side battle for promotion to League Two. Picture: Dan Istitene/Getty Images Photo: Dan Istitene
12. Duncan Turnball - Free Agent
The goalkeeper was released by Pompey with one EFL Trophy appearance to his name. Since then, he's remained without a club. Picture: Bryn Lennon/Getty Images Photo: Bryn Lennon