The clock is quickly ticking down to the official opening of the January transfer window - and it’s fair to say the Fratton faithful are eagerly waiting to see what the Blues’ recruitment team have up their sleeves this year.
Last term’s winter window proved a huge success, with the eight new signings introduced to John Mousinho’s first-team ranks helping Pompey move clear of the threat of relegation with two games of the season to spare.
A similar success story would be very much welcome next month as the Blues sit third from bottom in the Championship table going into their hugely-important fixture against Charlton at Fratton Park tonight.
But history shows not all signings work out as anticipated.
With that in mind, we asked AI to name what it considers to be Pompey’s best January arrivals - and who it believes ranks as the club’s worst.
Here’s what it came up with. See if you agree or disagree. Or whether you can think of better examples.

13. Worst: Tyler Walker (January 2022)
Details: Joined on loan from Coventry until the end of the season. Pompey appearances: 15 (1 goal) Departed: Summer 2022 - Coventry return. What AI has said: A loan striker who failed to score many goals and looked disinterested at times — widely seen as a flop during his spell. | Iconic Media Photo: Jason Brown

14. Best: Rob Atkinson (January 2025)
Details: Joined on loan from Bristol City until end of the season. Pompey appearances: 15 (2 goals) Departed: Summer 2025 - returned to Bristol City. What AI has said: He brought calm, physicality, and leadership to a defence that badly needed stability at the time. | Getty Images

15. Worst: Denver Hume (January 2022)
Details: Joined on permanent deal from Sunderland for an undisclosed fee. Pompey appearances: 31 (0 goals) Departed: Summer 2024 - Grimsby (undisclosed). What AI has said: Signed for a fee but never really established himself and eventually left two years later, making his arrival a poor piece of business. | The News

16. Worst: Charlie Daniels (January 2021)
Details: Joined on free transfer from Shrewsbury. Pompey appearances: 18 (1 goal) Departed: Summer 2021 - Colchester United (free transfer). What AI has said: Daniels is often cited as one of the least impactful mid-season arrivals under certain managers. Photo: Alex Burstow

