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...
1. Sylvain Deslandes - January 2018
Signed on loan by Kenny Jackett from former club Wolves in January 2018, yet the left-back failed to impress. He was handed just two appearances and, tellingly, was substituted around the 60-minute mark in each. Last heard of playing in the Azerbaijan Premier League for Sabail. Photo: Joe Pepler
2. Steve Seddon - January 2020
With Lee Brown injured, Kenny Jackett recruited Birmingham City left-back on loan in January 2020 as a replacement. The youngster provided some swash-buckling attacking displays from full-back and swiftly became popular among the Fratton faithful, scoring in a 3-0 win over Rochdale. He managed to hold off Brown upon his return from injury, only for the season to be curtailed by Covid. With the League One play-off campaign eventually taking place, he was overlooked for the first leg against Oxford, before starting the second leg, which ended in a penalty shoot-out defeat. Photo: Robin Jones
3. Aiden O'Brien - January 2022
The Republic Of Ireland international cancelled his contract with Sunderland in order to make a permanent move to Pompey on a six-month deal. O'Brien instantly became a fans' favourite after scoring with his first touch on his Fratton Park debut and then his maiden full outing for the club in a blistering start. With three goals in his opening four matches, O'Brien also impressed with his strong running, passion and desire, although spent more time on the bench than starting. Finishing with five goals in 15 outings, he spoke of his wish to sign a new deal in the summer of 2022, yet Cowley had little appetite and O'Brien has since featured for Shrewsbury, Gillingham and Salford. Photo: Paul Thompson
4. Anton Walkes - January 2018
Initially signed on loan from Spurs in January 2018 and marked his Blues bow with a goal on his debut against Doncaster in a 2-2 draw. Recruited permanently in the summer of 2018, Walkes was a versatile performer who proved his worth operating at right-back, centre-back, left-back and as a holding midfielder. Featuring in the 2019 Checkatrade Trophy-winning side, he totalled 66 appearances and three goals before leaving for Atlanta United in January 2020. He tragically died in a boat collision in January 2023. Photo: Joe Pepler