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.
5. 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: -
6. 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
7. Kal Naismith
After 94 appearances and 21 goals, the League Two title winner departed Pompey in the summer of 2018 as a free agent after a new deal could not be agreed. It has to be said, though, that Naismith - who is now at Championship Bristol City - was eager to test himself elsewhere. Photo: PinPep Media / Joe Pepler
8. Brett Pitman
The striker scored 41 goals in 99 appearances for Pompey. The former club skipper left under a cloud, after being told to train on his own during pre-season in 2020. That echoed the striker’s fate at the turn of the year, when he was instructed to train away from Pompey’s training ground. Speaking before his September 2020 free transfer move to Swindon, manager Kenny Jackett said: 'We have forwards, the likes of Reeco (Hackett-Fairchild) has a chance and an opportunity as well. We are quite well off for forwards at the moment. It’s not necessarily about Brett being out of contract soon. It’s just my choice on the group and the squad, as it is at the moment.’ Photo: Daniel Chesterton