With Portsmouth seven points adrift of the automatic promotion places, the next two games against their direct promotion rivals should have gone a long way to deciding just how successful Paul Cook and his team would be.
First up was Luton's visit to Fratton Park and the game was mired by a controversial incident when Cameron McGeehan's leg was broken in a 50/50 challenge with Michael Doyle.
Some fans continued to abuse the Luton midfielder who was booked for his protests and insults towards the home crowd which did nothing to endear him to the Pompey fans.
Hatters manager Nathan Jones seemed to be more upset with the home crowd rather than his own team as the game was settled by a Christian Burgess header, with Gary Roberts blasting a late penalty into the Fratton End for good measure.
Highlights: League Two Matchday 24: Portsmouth 1 Luton Town 0
That result, coupled with defeats for Carlisle and Plymouth, meant Pompey had closed the gap on the top three ahead of a televised clash with new league leaders Doncaster.
Unfortunately some sloppy defending gave Rovers an early lead as an unmarked John Marquis headed the ball past David Forde from close range.
Pompey mustered an equaliser when Kyle Bennett weighted a perfect through-ball for Kal Naismith who slotted the ball past Marko Marosi who had made some key saves to keep his side in it beforehand.
Any hopes of getting a result from the game were dashed as the Blues left themselves short at the back which allowed Tommy Rowe to smash the ball past Forde who should have probably saved his shot. Marquis then bagged a second goal for Donny which put the outcome beyond doubt.
Highlights: League Two Matchday 25: Doncaster Rovers 3 Portsmouth 1
That result left Pompey ten points behind Donny with an inferior goal difference which supposedly rendered them uncatchable with second place being the best the supporters could hope for.
The next match against Leyton Orient at Fratton Park was one which Paul Cook simply had to win despite the O's being Pompey's bogey team and having a few ex-Blues in their side.
Conor Chaplin had an early penalty saved as Pompey squandered their third straight spot kick in a row but the man made amends a minute later by tapping in Carl Baker's square ball at the far post.
Despite being dominated, Orient equalised out of nowhere as Gavin Massey curled the ball into the top corner from the edge of the box. Thankfully, Chaplin scored his second of the game by heading in another Baker delivery and the three points were secured.
Highlights: League Two Matchday 26: Portsmouth 2 Leyton Orient 1
Jamal Lowe had made his eagerly awaited debut in that match and played his part in the winning goal. He was then joined by fellow Hampton & Richmond striker Nicke Kabamba who was signed from the non-league club.
Milan Lalkovic was allowed to leave Portsmouth on loan at Notts County for the rest of the season ahead of Pompey's next match at Crawley.
However, the game at Broadfields was called off due to a frozen pitch. Baring in mind how pivotal the rearranged fixture was in Pompey's season, one wonders how the campaign would have played out if the game was played when it was originally scheduled to be.
Instead, Pompey were given a break ahead of away day specialists Exeter coming down to Fratton Park for January's final match.
What transpired was an awful performance in a poor match that Exeter won thanks to the ball kindly breaking to an unmarked David Wheeler in the box who lashed the ball past Forde.
Highlights: League Two Matchday 28: Portsmouth 0 Exeter City 1
That result saw more fans call for Paul Cook's head but his response was to strengthen the squad on transfer deadline day as Eoin Doyle finally made his loan move from Preston official and Aaron Simpson was borrowed from Wolves.
There were departures too as Michael Smith and Ben Close were loaned to Northampton and Eastleigh respectively whilst Adam Buxton had his contract terminated by mutual consent.
That marked the end of a busy January for Pompey, with an even busier February on the horizon.