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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9. James Vaughan - MISS
Joined on loan from Wigan and failed to score in three starts and eight outings off the bench. Spent half of his time back with his parent club. Photo: Joe Pepler
10. Omar Bogle - MISS
Four goals from eight starts and six outings off the bench wasn't a bad return, but didn't hit the highs many Pompey fans hoped for. Now with Doncaster Rovers where appearances have been fleeting. Photo: Joe Pepler
11. Viv Solomon-Otabor - MISS
Will forever be associated with the offside goal against Peterborough which proved so key to Pompey missing out on automatic promotion. Rapid but inconsistent across 10 appearances and one goal. Now with St Johnstone in the SPL. Photo: Joe Pepler
12. Duncan Turnbull - MISS
Rookie American made a single appearance last season and shipped five at Peterborough. A good size but not ready for the English game. Now with Las Vegas Light in the USL Championship. Photo: Nigel Keene