A number will have benefitted Pompey financially, with offers for the likes of Matt Clarke, Marcus Harness and Jamal Lowe too good to turn down.
Others, though, will have raised a few eyebrows and left many supporters disappointed.
Indeed, there’s quite a few departures that make you wonder ‘what if?’ if more of an effort had been made to retain certain individuals.
Here are 18 former Pompey players we believe fit into that latter category since the Blues returned to League One in 2017.
. Collage Maker-28-Mar-2023-05-20-PM-8035.jpg
From left: Nathan Thompson, Jack Whatmough, Conor Chaplin and Ben Thompson Photo: National World
. Enda Stevens
The left-back never featured for Pompey in League One, despite helping the Blues to the 2016-17 League Two title. He left for Sheffield United on a free transfer soon afterwards as the club put off contract talks until the end of that season. By that stage, the Irishman was being coveted elsewhere. Photo: ADRIAN DENNIS
. Michael Doyle
Like Stevens, inspirational Pompey captain Doyle left on a free transfer after guiding the Blues to the League One title. The combative midfielder left the Blues to be closer to his Midlands-based family, returning to former club Coventry. But did Pompey do enough to convince him to lead the club in League One? Photo: Harry Murphy
. Gary Roberts
The attacking midfielder's 20 goals in 80 appearances made him a firm fans' favourite during his two seasons at the club. However, just months after winning League Two with Pompey, he was instructed to train with the academy by new boss Kenny Jackett. Roberts reached a mutual agreement to cancel his contract in August 2017 to join Wigan. There he won the League One title, before enjoying two seasons in the Championship. Photo: Harry Murphy
. Christian Burgess
The defender joined Belgium outfit Union Saint Gilloise on a free transfer in 2020. His stock had soared following the best Blues season of his five years with the club, prompting suitors from home and abroad. Similarly, they were offering deals longer than what Burgess anticipated receiving at Fratton Park. And following a scintillating season, the potential of a 12-month contract was deeply unpalatable. Could Pompey have brought the out-of-contract centre-back to the negotiating table far earlier, particularly before his head was turned? Photo: -
. Conor Chaplin
The former Blues academy youngster said he didn’t want to leave Fratton Park in the summer of 2018. However, Chaplin felt it was the best thing for his long-term career, after failing to convince Kenny Jackett he should be a first-team regular. The striker, who scored 25 goals in 122 appearances for Pompey, has since gone on to establish himself as a firm favourite at Coventry, Barnsley and Ipswich. His 19 goals for the Tractor Boys this season has them challenging for automatic promotion back to the Championship. Photo: Bluepitch Media / Joe Pepler
1. Collage Maker-28-Mar-2023-05-20-PM-8035.jpg
From left: Nathan Thompson, Jack Whatmough, Conor Chaplin and Ben Thompson Photo: National World
2. Enda Stevens
The left-back never featured for Pompey in League One, despite helping the Blues to the 2016-17 League Two title. He left for Sheffield United on a free transfer soon afterwards as the club put off contract talks until the end of that season. By that stage, the Irishman was being coveted elsewhere. Photo: ADRIAN DENNIS
3. Michael Doyle
Like Stevens, inspirational Pompey captain Doyle left on a free transfer after guiding the Blues to the League One title. The combative midfielder left the Blues to be closer to his Midlands-based family, returning to former club Coventry. But did Pompey do enough to convince him to lead the club in League One? Photo: Harry Murphy
4. Gary Roberts
The attacking midfielder's 20 goals in 80 appearances made him a firm fans' favourite during his two seasons at the club. However, just months after winning League Two with Pompey, he was instructed to train with the academy by new boss Kenny Jackett. Roberts reached a mutual agreement to cancel his contract in August 2017 to join Wigan. There he won the League One title, before enjoying two seasons in the Championship. Photo: Harry Murphy