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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5. Connor Ronan - MISS
Showed glimpses of quality and possessed obvious talent but wasn't physically developed and but overall failed to make an impact after arriving on loan from Wolves in the transfer window of January 2018. Photo: Joe Pepler
6. Anton Walkes - HIT
Anton Walkes made 66 appearances during two years at Fratton Park after arriving from Spurs in January 2018. A solid performer rather than spectacular. The amount of football he got under his belt in 18 months makes him more of a hit than miss. Photo: Daniel Chesterton
7. Stephen Henderson - MISS
Just the one appearance second time around after arriving on loan from Nottingham Forest. Has continued to be a back-up keeper since and is currently with Charlton. Photo: JPIMedia
8. Bryn Morris - MISS
Injury-ravaged time and took some awful flak from fans. A total of 28 appearances in two-and-a-half years tells a story. Now out of favour at Burton Albion. Photo: Joe Pepler