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.

5. Worst: Lloyd Isgrove (January 2019)
Details: Joined on loan from Barnsley until end of the season. Pompey appearances: 0 (0 goals) Departed: Summer 2019 - returned to Barnsley. What AI has said: Arrived amid hopes of bolstering the squad but didn’t play a single match, making him one of the least effective January recruits in recent memory. | National World

6. Best: Andres D'Alessandro (January 2006)
Details: Joined on loan from Wollfsburg until end of season. Pompey appearances: 13 (1 goal). Departed: Returned to Wolfsburg at end of season, then signed for Real Zaragoza. What AI has said: Although on a short loan, the Argentine playmaker was brilliant during his stint, providing creativity and influence as Portsmouth battled top-flight survival. His brief spell is still fondly remembered for lifting the team’s performances. | Getty Images

7. Worst: Viv Solomon-Otabor (January 2019)
Details: Joined on loan from Birmingham until end of the season. Pompey appearances: 10 (1 goal) Departed: Summer 2019 - returned to Birmimgham. What AI has said: Another loan signing during a crucial promotion push, Solomon-Otabor struggled for form and had little positive impact, contributing to the window being widely criticised. | Getty Images

8. Best: Hayden Carter (January 2022)
Details: Joined on loan from Blackburn Rovers until end of season. Pompey appearances: 22 (1 goal). Departed: Returned to Blackburn Rovers, where he remains. What AI has said: Arrived from Blackburn Rovers and became a mainstay in defence, earning regular starts and solid performances through the second half of the season. Photo: Paul Thompson

