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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17. George Byers - MISS
Big hopes and clear quality on the ball, but was frustratingly overlooked by Kenny Jackett and restricted to just four league starts amid 15 appearances after joining on loan from Championship Swansea. Now with League One rivals Sheffield Wednesday. Photo: Joe Pepler
18. Charlie Daniels - MISS
What happened there? Much was anticipated but father time seemed to rapidly catch up with the former Premier League man amid 18 appearances and a disappointing Fratton Park stay. Photo: Joe Pepler
19. Lewis Ward - MISS
Came in as a cheap backup option and didn't get an appearance under his belt, after signing on loan from Exeter. Has now joined League Two Swindon where he's made seven appearances. Photo: Jason Brown
20. Harvey White - MISS
Made 22 appearances, but only got five starts in the league. Showed real potential, bagged a great header at Oxford and the feeing is the Spurs loanee could have been a hit if he'd been given more of an opportunity. Photo: Jason Brown