It’s an overhaul of the playing squad which head coach Danny Cowley thought was necessary – and yet more could follow as the Blues remain open to offers for those who remain.
Some of those 14 have found new clubs, some will remain at their parent clubs after a short stint at Fratton, while others’ future’s remain up in the air.
So what has happened to those let go by Pompey since that crushing 1-0 defeat at the hands of Accrington on May 9? Is there more to come, with the transfer window still stuck in second gear?Here, we find out...
9. Bryn Morris (Central Midfield)
Although Morris is still technically contracted to Pompey until the end of the month, his exit was sealed back in January when he joined Northampton on loan. That's given him plenty of time to sort out his future - and that's exactly what he has done. The 25-year-old will rejoin Burton Albion on July 1, after agreeing a two-year deal with the Brewers. Photo: Joe Pepler
10. Ryan Williams (winger)
The winger expressed a desire to stay at Fratton Park - but just like Whatmough, Close and Naylor, the Aussie was offered the chance to remain but on reduced terms. Those terms were never agreeable, as far as Williams was concerned. He's since joined League One rivals Oxford on a free transfer, signing a two-year deal at the Kassam Stadium. Photo: Simon Davies
11. Craig MacGillivray (Goalkeeper)
MacGillivray's Pompey future remains open to interpretation among sections of the Fratton faithful. But the facts are last season's News/Sports Mail player of the season has not been offered the chance to extend his Blues career. Pompey are in the market a new keeper - while the Scot is in the market for a new club. Both Ipswich and Charlton have been mentioned as possible destinations, although the Addicks looks a more likely new home for the 28-year-old. Photo: JPIMedia
12. Tom Naylor (Central midfield)
Pompey's former captain looks dejected in this picture after the Blues' home defeat to Blackpool back in February. It was a familiar pose by the midfielder as Pompey's promotion hopes took blow after blow until it was officially lights out against Accrington on the final day of the season. Naylor, though, was all smiles earlier this month when details of his three-year deal at Wigan was announced - a move which will become official on July 1 upon the expiry of his Blues contract. Photo: Joe Pepler