At present, the Blues have no senior front men registered going into next season, with last season’s attackers’ loans and deals expiring.
Aiden O’Brien has been offered fresh terms, while Danny Cowley is hoping to bring George Hirst back after his successful loan spell last term.
Nevertheless, the Fratton chief is still searching for reinforcements to boost his side’s promotion credentials in 2022-23.
This is nothing new for the club’s head coaches, though, as predecessor Kenny Jackett often reinvented his striking department in bid to return to the second tier.
Ultimately, his pursuit proved fruitless as his picks often failed to live up to expectations.
But who all have been signed since 2017? And how have they fared since they departed Fratton Park?
Here’s what we found out
5. Nicke Kabamba - signed from Hampton & Richmond Borough
Signed by Paul Cook in January 2017, Kabamba made one League One appearance in 2017-18 before a loan move to Colchester. Spells at Aldershot, the Hawks, Hartlepool, Kilmarnock and Northampton followed before he spent the second half of last season on loan at Woking. Picture: Joe Pepler Photo: Joe Pepler
6. Conor Chaplin
Chaplin played the entirety of the first season back in League One -- making 32 appearances while scoring five goals. He was allowed to head out on loan to Coventry at the start of the 2018-19 season before that switch was made permanent the following January. A move to Barnsley followed shortly afterwards, but after two successful years with the Tykes, Chaplin was reunited with former Blues Paul Cook at Ipswich last summer where he scored 11 goals in 47 outings. Picture: Joe Pepler. Photo: Joe Pepler
7. Joe Mason – signed from Wolves (on loan)
Mason's disastrous time at Pompey was summed up by his missed penalty against Crawley in the EFL Trophy. The striker made only one league appearance for the club before returning to Wolves in January 2019. A permanent move to MK Dons followed, before he moved across the globe to Canadian side Cavalry FC – where he is now gunning for the league title. Picture: Joe Pepler Photo: Joe Pepler
8. James Vaughan – signed from Wigan (on loan)
Vaughan was one of those entrusted to fire Pompey to League One glory in January 2019, but failed to score in 10 league appearances as the Blues lost to Sunderland in the play-offs. Spells at Bradford and Tranmere followed, before he retired in 2021. Now he’s Rovers' sporting director. Picture: Joe Pepler Photo: Joe Pepler