It will be a crucial period for Danny Cowley to replenish and reshape his options with his side in play-off contention.
But it’s also a period fraught with difficulties and danger, when it comes to identifying the right players who could make a difference.
Over the past five seasons, the Blues have brought in 22 players at the turn of the year – with plenty of additions disappointing in that time.
There’s also been a few runaway successes, too, so we’ve trailed through Pompey’s January business and decided if transfer gems were landed – or were they dud signings….
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13. Cameron McGeehan - MISS
Much was hoped for what the midfielder could achieve over the second half of the 19-20 season. Made 17 appearances and scored two goals but didn't quite reach the levels anticipated - and of course missed the crucial penalty in the play-offs at Oxford. Photo: Joe Pepler
14. Eoin Doyle - MISS
Pompey pushed the boat out to land the striker on loan from Preston, but could only return two goals in 12 appearances as Kal Naismith took centre stage on the run to the League Two title. Photo: Joe Pepler
15. Steve Seddon - HIT
Many Pompey fans are still pining for the left-back who made such an impact on loan from Birmingham. Plenty of talk about a permanent deal but his parent club demanded too big a fee. Joined Oxford United for an undisclosed fee last summer instead. Photo: Daniel Chesterton
16. Reeco Hackett - MISS
This shout was on a knife-edge after 24 outings this term. But has featured just once previously and was farmed out to Bromley and Southend. By the end of this season the winger could well be a hit, if his form continues. Photo: Stephen Flynn