Rumours circulated over the lack of playing time for some (usually with good reason!) while others simply found their Fratton stays hindered by injuries.
So we’ve delved into the Blues’ past to remember those we wanted to see in action – but never quite got the opportunity to watch in all their glory.
5. Mladen Rudonja
Turbo Rudi was signed with a reputation for leaving defences in his slipstream. It was his Pompey career which went up in smoke, though, with just four starts in two years. Photo: Julian Herbert
6. Stanley Aborah
Aborah only managed to make 122 minutes worth of action during the 2016-17 campaign and would go on to quit football that summer. Photo: Joe Pepler
7. Mike Williamson
Mystery surrounded the £3m arrival of Williamson from Watford with the club on the brink of financial meltdown. Williamson never played a game and was sold off to Newcastle five months later. Photo: Dave Haines
8. Roudolphe Douala
Cameroon speedster caused havoc for Sporting Lisbon, but then started just a single game in the 2006-07 season. 'If I just needed someone who's quick I would've signed Linford Christie,' was one Harry Redknapp's comments on the winger. Photo: The News