Paul Cook had concluded his transfer deadline day business and his attention turned to a tricky encounter with Wycombe at Adams Park.
Pompey missed a few great opportunities to score and were duly punished by a flukey deflected Scott Kashket goal in the second half as the Blues fell to back-to-back defeats.
That result meant that Portsmouth had fallen a whopping 17 points behind leaders Doncaster but more importantly they looked vulnerable to finishing outside of the play-off places altogether.
This caused the more vocal Pompey fans to yet again call for Cook's head and get someone in who could "fix the situation" despite the rest of the month's fixtures looking favourable. The first of those was the visit of Accrington to Fratton Park where anything but a win would have meant chaos.
Matt Clarke got the home side off to the perfect start by heading in a goal after just a minute of the match had passed but that wasn't a catalyst for a goal glut as Pompey struggled to create chances despite not being threatened by Stanley.
It took until stoppage time for the result to be confirmed as Gary Roberts led a counter-attack and supplied Kal Naismith with the ball who slotted home the second goal to get the Blues back to winning ways, even if the performance wasn't enough for some of the harshest critics at Fratton Park.
Valentine's Day saw Pompey return to their home turf to take on Blackpool under the floodlights and the old ground was rocking to create one of the best atmosphere's of the season.
The performance matched, too, as a dominant Portsmouth took the lead thanks to a strike from Gareth Evans from Enda Stevens' cross. Stevens then made a superb challenge in the second half to deny the Tangerines what looked to be a certain goal.
Again, it took until stoppage time to confirm the result as Eoin Doyle held the ball up well before combining with Carl Baker to slot in his first Pompey goal from close range.
Paul Cook added Stanley Aborah to his squad whilst consecutive wins had Pompey fans beginning to be optimistic about their team's chances of promotion once again but they received a reality check when Saturday arrived and many of them travelled to The Hive for the fixture against Barnet.
A truly dreadful game looked as if it would end in defeat after David Forde allowed Mauro Vilhete's free kick to sail past him but up popped Conor Chaplin to unleash a late screamer to equalise for the visitors as they escaped north London with a draw. That would be Chaplin's last goal of the season.
That point was enough to stay in touch with the following opposition in Carlisle United. The Cumbrians had won their previous two matches to halt an alarming slump in form but Pompey knew that they would be in prime position for automatic promotion if they could beat them at Brunton Park.
After a goalless first half which saw both of Carlisle's centre backs injured, Pompey stepped up their game and Gary Roberts broke the deadlock with a wonderful finish having been crowded by Cumbrians.
Amine Linganzi then hammered home a second whilst Jack Whatmough scored his first goal for the club to earn Portsmouth a comprehensive and crucial win over their promotion rivals.
That result meant for the first time since the early stages of the campaign, Portsmouth could finish the next matchday in the automatic promotion places if the Cumbrians lost again and Pompey could defeat mediocre Morecambe.
Unfortunately the match against the Shrimps turned into a wasted opportunity as although Naismith scored with a shot from distance as soon as he came on, some sloppy defending allowed Lee Molyneux the space to fire in an equaliser from an angle.
A win would have been enough to catapult Paul Cook's men into the top three after Carlisle and Plymouth both lost but there would be another golden opportunity to move into the automatic promotion places with those sides playing each other the forthcoming Saturday.
All Pompey had to do was beat Crewe Alexandra at Fratton Park who had just been thrashed 4-0 by Hartlepool...