Pompey's first task of November was to progress in the competition they had won in 2008 and reached the fourth round in last season.
The Blues were handed an uninspiring home draw against Wycombe and that lack of enthusiasm obviously transmitted to the players as they produced a lacklustre performance at Fratton Park.
David Forde once again came out of his goal for a free kick he was never going to reach and the confusion in the box allowed Paris Cowan-Hall th easy task of nodding the loose ball into an unguarded net.
Gareth Evans converted Enda Stevens' cross at the start of the second half for the equaliser but another long ball into the box was met by Adebayo Akinfenwa as his header looped over Forde and into the net. Pompey couldn't force a replay and were knocked out of the F.A Cup at the first hurdle for the sixth time in seven seasons.
Highlights: F.A Cup Round 1: Portsmouth 1 Wycombe Wanderers 2
The next match saw a new post-war record low attendance of just 1,200 watch the Checkatrade Trophy match with Bristol Rovers, breaking the record of 1,355 set the previous month against Reading Reserves.
Michael Smith's early penalty was saved but a late screamer from the impressive Kal Naismith earned Pompey a win. However, Yeovil's win over Reading B meant the Blues were knocked out of the farcical compettion and the majority of fans rejoiced.
Highlights: Checkatrade Trophy Matchday 3: Portsmouth 1 Bristol Rovers 0
With his team out of the cups, an under pressure Paul Cook was able to completely focus on the league as Mansfield arrived at Fratton Park looking to further increase the heat on the Pompey manager.
However, the nerves were settled early on when Kyle Benett was fouled in the box by Matt Green and Gary Roberts blasted the resulting spot kick down the middle of the goal.
When Kyle Howkins was dismissed early in the second half for a late lunge on Bennett, the home fans were expecting a goal glut and it never came. Instead, portions of the ground began to voice their frustrations with Pompey playing possession football against ten men.
The boos continued even when the Stags were reduced to nine men after Alex Iacovitti received a straight red card for a high challenge on Michael Doyle as Paul Cook's men continued to play a tentative game.
However, when Noel Hunt converted Naismith's cross with eight minutes to go, Mansfield finally crumbled and Carl Baker bagged another two goals in stoppage time with strikes from outside the box to confirm what was probably the worst received 4-0 win in the history of football.
Highlights: League Two Matchday 16: Portsmouth 4 Mansfield Town 0
Pompey were hoping to follow that win with another at Cheltenham and had plenty of chances to take the lead only to be denied by goalkeeper Russell Griffiths and the woodwork on numerous occasions.
Predictably, the Robins took the lead as some what was becoming trademark poor defending from a long free kick into the box resulted in Daniel O'Shaughnessy scoring his first goal in games involving Pompey and Cheltenham this season.
Gary Johnson's struggling side looked like they were going to take all three points but a late equaliser came when Smith pounced on a loose ball from close range as the teams shared the spoils at Whaddon Road.
Highlights: League Two Matchday 17: Cheltenham Town 1 Portsmouth 1
There wasn't much time to reflect on what was a disappointing draw as a promotion six-pointer folllowed at Luton on the upcoming Tuesday night.
It seemed like Pompey would fail another one of their important tests of the season when, despite Gareth Evans needing treatment on the floor, Danny Hylton headed in Alan Sheehan's cross and were only denied a second goal by the offside flag.
But then came the Portsmouth comeback as Smith struck in an equaliser into the bottom corner from distance and Evans turned the game on its head by finishing off a corner routine.
Naismith slammed in a third goal to confirm Pompey's most impressive performance of the season and their most important win. Luton acknowledged that they were outplayed and Paul Cook's men leapt their opponents in the League Two table and were just a single point behind the top three.
Highlights: League Two Matchday 18: Luton Town 1 Portsmouth 3
If Pompey could build on such a positive result at Kenilworth the following weekend then the month would have ended on a high and everyone would have believed that the Blues were capable of mustering a title challenge.
However, things seemed to come apart during the match with Stevenage at Fratton Park. With the scores goalless at half-time, neither Christian Burgess or Michael Doyle emerged after the break as it transpired that they had a bust up in the dressing room.
That obviously had an effect on the team as some comical defending allowed Steven Schumacher to score from the edge of the box and then some shocking marking in the area allowed Matt Godden to add a second goal.
Smith pulled one back but Pompey couldn't find an equaliser and were condemned to a fourth defeat in five home games. Some fans were citing a Fratton Park crisis as the inquisition into Paul Cook's managerial capabilities and the overall team spirit was called into question.
Highlights: League Two Matchday 19: Portsmouth 1 Stevenage 2
That result left Pompey in fourth place going into the final month of 2016 with plenty of questions to be answered as the season headed into its tough winter months.