Glen Johnson, Peter Crouch, Sylvain Distin, Younes Kaboul and Prince Boateng.
Now the list of Pompey’s biggest sales during the last decade features a fresh addition – Matt Clarke.
On Friday, the 22-year-old was recruited by Brighton in a deal worth around £4m, potentially reaching in excess of £5m.
And that move ensures Clarke is among Pompey’s top-six transfer fees received since the summer of 2009.
Certainly the central defender is among esteemed company consisting of FA Cup winners, internationals and, in Boateng’s case, a champion in Serie A and La Liga.
Still, Clarke represents Pompey’s largest fee received since Boateng’s £5m exit to Genoa in August 2010.
And in terms of the past 10 years, he finds himself sixth on the roll of honour.
Looking back, July 2009 signified the start of the Blues’ demise, with a frenetic clear-out of prized assets during the final throes of the Sacha Gaydamak era.
With Pompey desperate for cash to fend off administration, Johnson (£17m) moved to Liverpool and Crouch (£10m) headed to Spurs.
Before August had ended, Distin (£5m) joined Everton and Niko Kranjcar (£2.5m) followed Harry Redknapp and Crouch to White Hart Lane.
During the January 2010 transfer window, with Avram Grant now manager and the Ali Al Faraj ownership heading into the hands of Balram Chainrai, more sales followed.
Kaboul (£6.5m) returned to Spurs, a figure significantly reduced on the basis of Pompey still owing the White Hart Lane club for the original transfer, plus a sell-on clause.
There was also the chaotic deal which took Asmir Begovic (£3.25m) to Stoke, with the Blues handing £1m to Spurs as a sell-on clause after originally agreeing a deal with them.
Following defeat in the FA Cup and relegation to the Championship at the end of the 2009-10 campaign, another clear-out took place.
Nadir Belhadj (£3.5m) and Papa Bouba Diop (£250,000) both left Fratton Park in July 2010.
Then Boateng, following an eye-catching World Cup for Ghana, was sold to Genoa for £5m, although instantly loaned to AC Milan in another convoluted deal.
Now Clarke has joined such fine Pompey company, representing the sixth-highest transfer fee received in a decade.