Jamie Ashdown and Ricardo Rocha have been told they do not have a Pompey future.
The pair have not been offered new contracts as Michael Appleton seeks to overhaul his squad for life in League One.
Rocha is a firm fans’ favourite and a first-team regular, while Ashdown is the Blues’ longest-serving player.
However, with the club’s desire to drive down wages and look in a new direction, Appleton decided against giving fresh deals.
The pair were informed of the decision by the Pompey manager and join Benjani in leaving the club since the season’s end.
It is another indication of Appleton’s intent to rebuild the Blues from scratch.
Rocha and Ashdown both live locally and are well settled at Fratton Park but the Pompey boss has elected to ring the changes.
Crucially for the club, the decision will assist in reducing the £11m wage bill towards the club’s £5m target.
But it is understood neither were among the Blues’ top earners.
Ashdown made 123 appearances after arriving on a free transfer from Reading in the summer of 2004.
He was released in the summer of 2010 but returned months later under Steve Cotterill – penning a two-year deal and going on to appear in all 50 matches in the 2010-11 campaign.
The keeper won several player-of-the-year awards in the process and started this season as number one.
But he lost his place to Stephen Henderson in October before reclaiming it when the Irishman joined West Ham.
Off the pitch, along with his wife, Zoe, Ashdown has been inspirational in getting players to pledge to the Pompey Trust share scheme.
To date, the pair have recruited 13 names, including Jason Pearce, Joel Ward, Luke Varney, David Norris, Gary O’Neil – and Rocha.
Defender Rocha was one of the key figures in the side who reached the FA Cup final against Chelsea in 2010.
Since arriving in February 2010, he has gone on to establish himself as a huge Fratton favourite with his composed displays in defence.
His performances this season were recognised by the Northern Blues supporters’ club, who presented him with their player-of-the-year award before the season’s last home match.
The softly-spoken 33-year-old was also named by his team-mates as the players’ player of the season.
In total, Rocha made 76 appearances for the Blues but never scored.
Along with Benjani, they were the only three first-team players out of contract this summer.