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.

9. Worst: Omar Bogle (January 2019)
Details: Joined on loan from Cardiff until end of the season. Pompey appearances: 15 (4 goals) Departed: Summer 2019 - returned to Cardiff. What AI has said: Started brightly with goals in his first games, but his scoring dried up and he faded badly as the season progressed, leaving the team with a thin return on investment. | PinPep Media / Joe Pepler

10. Best: Aiden O'Brien (January 2022)
Details: Joined on free transfer from Sunderland on deal until end of the season. Pompey appearances: 17 (5 goals) Departed: Joined Shrewsbury on free transfer following expiry of Pompey contract. What AI has said: Came in mid-season and made an immediate impact with goals and energy, quickly becoming a fan favourite during his short stint. | Iconic Media

11. Worst: Bryn Morris: (January 2019)
Details: Joined on a permanent deal from Shrewsbury for an undisclosed fee. Pompey appearances: 28 (1 goal) Departed: Summer 2021 - Burton Albion (free transfer). What AI has said: Brought in permanently to add midfield strength, but persistent injury problems hampered his time at Pompey and he never delivered the expected influence. Photo: Joe Pepler

12. Best: Anton Walkes (January 2018)
Details: Joined on loan from Spurs until the end of the season. Pompey appearances: 12 (1 goal) Departed: At end of his loan spell but returned on a permanent deal that summer for £200,000. What AI has said: Initially a winter window loan from Tottenham, Walkes impressed right away, scoring on his debut and eventually earning a permanent move. He became a versatile and valued squad member over subsequent years. | Getty Images

