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?
1. Oli Hawkins – signed from Dagenham & Redbridge
Hawkins will be mostly remembered for his time at Pompey for his winning penalty kick in the 2019 EFL Trophy final against Sunderland rather than his 18 goals in 96 appearances. During his final season at the club, he often played at centre-back before his departure to Ipswich in 2020. After a season at Portman Road, he left for Mansfield where he is set to play in the League Two play-off final. Photo: Joe Pepler
2. Brett Pitman – signed from Ipswich
Arguably the most successful striker on the list, Pitman became a fans’ favourite during his three years at Fratton Park. He scored 41 goals in 99 appearances in royal blue, but has failed to match his prolific form since his 2020 departure. Spells at Swindon and Bristol Rovers did not go to plan - neither did his loan move to Eastleigh last season, where he scored one goal in 17 appearances before his return to The Gas. Picture: Daniel Chesterton/phcimages.com/PinPep Photo: Daniel Chesterton
3. Louis Dennis – signed from Bromley
A forgotten man from the 2018 transfer window, Dennis made only eight appearances for Pompey while scoring once. After only one season at the Blues, he joined Leyton Orient, before returning to Bromley in 2021. Last term he scored once in 23 outings but recently won the FA Trophy at Wembley. Picture: Joe Pepler Photo: Joe Pepler
4. Curtis Main - signed from Doncaster Rovers
The striker was a member of the squad who won promotion from League Two in 2017, but made only five appearances in the third tier in 2017-18 as Kenny Jackett made his mind up on Main very quickly. He then moved to Aberdeen and Shrewsbury before joining St Mirren last summer. Since then, he's scored four goals in 36 games. Picture: Joe Pepler Photo: Joe Pepler