Rich Hughes and John Mousinho are challenged to bolster a side which tops League One heading into the New Year, yet since 2017-18 it has often proven a frustrating window.
There have been some excellent signings, some awful ones and others simply bang average. So here’s a look at 16 of them from the previous six Januarys in League One...
5. Matt Macey - January 2023
Effectively John Mousinho's first signing as Pompey head coach, Macey's arrival was hardly warmly received by doubting supporters left unimpressive by the goalkeeper's playing history. However, the towering former Arsenal man proved an excellent loan capture from Luton, commanding his area well and demonstrating shot-stopping talent. Such was his favourable impact, he was on Pompey's radar again in the summer of 2023, but they instead opted for Will Norris. Photo: Jason Brown
6. Bryn Morris - January 2019
Shrewsbury recalled Morris from a successful Wycombe loan spell in order to sell him to promotion-chasing Pompey in January 2019. However, the luckless central midfielder suffered a catalogue of injury problems which significantly impacted his time at Fratton Park. Surprisingly replaced Tom Naylor in the 2020 League One play-off semi-finals against Oxford United. However, never impressed and left on a free transfer in July 2021 following 28 appearances and one goal. Departure date: July 21, 2021;
Transfer: Free (Burton);
Current club: Grimsby;
Appearances since: 10 apps, 1 goal (Grimsby), 10 apps, 0 goals (Burton - 2021-22 season), 11 apps, 1 goal (Hartlepool loan 2021-22 season). Photo: Joe Pepler
7. Omar Bogle - January 2019
Bogle dropped down from the Championship with Cardiff to join Pompey on loan for the remainder of the season and enjoyed an impressive start to life at Fratton Park. Having netted on his debut after coming off the bench in a 3-2 loss at Luton, he then scored on his full debut the following match against Doncaster. He would register four times in his opening eight appearances and also started the Checkatrade Trophy final victory over Sunderland. However, his season petered out, failing to score in Pompey's final 11 matches, of which he missed chunks through injury. Photo: Daniel Chesterton
8. Hayden Carter - January 2022
Proved a revelation after signing on loan from Blackburn in January 2022 under Danny Cowley. Utilised either at centre-back or right-back, Carter demonstrated he was an accomplished performer in either role as he made 22 consecutive starts until the season's end. Clearly destined for regular first-team football when he returned to Ewood Park and that has proven to be the case, having established himself as a Championship player. Photo: Paul Thompson