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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1. Aaron Simpson - MISS
Had more success on Love Island than at Pompey after arriving at the start of 2017. Photo: Joe Pepler
2. Nicke Kabamba - MISS
Wasn't quite ready for Pompey after stepping up from non league in 2017. Has gone on to do reasonably for Hartlepool and Kilmarnock and now with Northampton. Photo: The News
3. Jamal Lowe - HIT
Meteoric rise really kicked in at Pompey. Scored as promotion was sealed at Notts County and bagged spectacularly at Wembley against Sunderland. Now with Bournemouth after spells at Wigan and Swansea. Photo: Joe Pepler
4. Sylvain Deslandes - MISS
Another unimpressive six-month loan stay from Wolves which returned just two appearances. Photo: The News