Reeling from the home defeat to Stevenage, Pompey had to wait an extra week to put that result behind them due to their non-involvement in the second round of the F.A Cup.
In that time, Ben Tollitt made his loan move to Tranmere Rovers permanent before Portsmouth fans made the journey to Blundell Park for the first time since 2002 to watch their team take on Grimsby.
Pompey had the better of the game yet couldn't find that elusive goal with chances wasted. It seemed like there would be another two points dropped in the race for promotion until Carl Baker was brought down on the edge of the box with less than five minutes remaining.
Up stepped Kal Naismith to curl a beautiful free kick beyond the Grimsby goalkeeper and win the game for the visitors. It was a precious three points which saw the gap closed on the automatic promotion places.
Highlights: League Two Matchday 20: Grimsby Town 0 Portsmouth 1
Next up was a visit of struggling Hartlepool United, who had conceded nine goals in their previous two matches, to Fratton Park. It was going to be an easy victory for the resurgent Blues, right?
Wrong. Pools parked the bus and Paul Cook's men struggled to break them down and when they did, ex-Pompey keeper Trevor Carson was in the way to frustrate the expectant home crowd. The match ended in a goalless draw with an increasing number of fans questioning how the manager was going to win enough home games to attain promotion.
Highlights: League Two Matchday 21: Portsmouth 0 Hartlepool United 0
Those dropped points meant Pompey were seven behind the top three but they had the perfect opportunity to get back to winning ways with a trip to bottom-of-the-table Newport on Boxing Day.
The game didn't start in the way the visitors would have hoped as Josh Sheehan scored for the Exiles with a free kick bent past David Forde. Pompey fans who stayed at home were then spitting out their Christmas dinner leftovers as Rhys Healey tapped in a second goal after Forde spilled a shot.
Fans were furiously typing away on social media with the "Cook Out" brigade in full force but the comeback began when Danny Rose slotted in Gareth Evans' cross.
An oppurtunity to equalise was squandered when Naismith blasted a penalty over the bar but Pompey were on terms when Enda Stevens blasted the ball home after being picked out by Rose in the box.
And the turnaround was complete when Naismith made amends for his earlier spot kick woe by whipping a free kick into the box only for it to go straight into the net with nobody getting a touch on it.
The final whistle blew much to the relief of everyone in South Wales and Portsmouth. The twitter trolls were silenced for the time being as Paul Cook's men were forging a reputation of being away day specialists
Highlights: League Two Matchday 22: Newport County 2 Portsmouth 3
The final match of the year was a farcical contest at Huish Park as a thick fog descended over Yeovil meaning that the specatators could barely see a thing.
The game should never have taken place and it was unsurprising that the last match of 2016 ended in a goalless draw as Pompey extended their unbeaten record away from home to seven games.
Highlights: League Two Matchday 23: Yeovil Town 0 Portsmouth 0
With half of the season gone, Portsmouth were seven points off the automatic promotion places with many fans believing that if promotion was going to be achieved, they would have to win their next two crucial games against fellow promotion challengers Luton and Doncaster or face the play-offs again.
2017 would begin much in the same way as 2016 ended.