Unbeaten in October, Pompey looked to build on an encouraging month with more solid performances in the league and perhaps progress in the cup competitions too.
First up was the visit of Exeter City and their merry band of drummers to Fratton Park for one of the most entertaining, albeit tense, games of the season.
Portsmouth took the lead on the stroke of half-time when Ricky Holmes' cross somehow managed to find the back of the net with the aid of the wind. Ryan Bird headed in two goals in the second half to seemingly make the game safe for the hosts. Or not.
Danny Coles pulled one back for the Grecians and panic started to settle in with ten minutes of the match to go when John O'Flynn headed past Trevor Carson. Thankfully Pompey survived the siege but the cracks were there for all to see as matters on the pitch soon took a nose dive.
The following weekend saw Pompey fans make yet another trip to Stevenage, this time for an FA Cup tie. Francois Zoko scored twice to give Boro a commanding lead and it seemed like the game was over when Gavin Mahon was sent off.
However, that just seemed to get Pompey fired up as David Connolly pulled a goal back for the ten men. Whittingham's men pushed for an equaliser but it didn't come and Portsmouth's miserable record in the FA Cup since reaching the final in 2010 continued.
There was little time to contemplate being knocked out of the cup as another trophy was to be played for in midweek with a trip to Wales to face Newport in the Johnstone's Paint Trophy.
What followed as a sound beating from County as an embarrassing mistake from Bondz N'Gala saw him head the ball over Carson to allow Conor Washington a tap into an empty net. Deji Oshilaja doubled County's lead soon after as Carson could only parry a free kick into his feet for another easy finish.
Whilst the home side were reduced to ten men after David Pipe was sent off for a lunge on Holmes, they still looked like the more threatening side and ended a miserable night for the visiting fans when Washington scored on the break and Sonny Bradley's late consolation was ruled out for handball.
The performance that night was dreadful but there would be worse to come as Pompey took on AFC Wimbledon for the very first time and hit a new low.
Carson gave away a penalty before saving it (and the rebound) only for his defence to let him down as Andy Frampton turned in the opening goal with the initial shot saved.
The Dons doubled their lead when an unmarked Frampton headed the second goal in and Pompey fell apart with Sammy Moore and Michael Smith adding late goals to complete the humiliation. Fans left Kingsmeadow disgusted with messageboards going into meltdown, calling for Whittingham's head but the board didn't act as they believed that the Pompey cult hero could turn things around.
Scunthorpe were the next team to visit Fratton Park having just sacked Brian Laws and it seemed like Whittingham was going to silence his critics as Pompey took the lead courtesy of Tom Craddock's only goal of the season.
However, that lead didn't last long as more terrible defending allowed Dave Syers to score an easy equaliser and although Pompey put up something of a fight, Syers poached a winner for the Iron which saw the home fans boo their team off and voice their disapproval after a fourth straight defeat.
That was to be the final straw for the board who sacked Whittingham on the following Monday with results and performances way below the expectations of Portsmouth Football Club. Andy Awford was given the caretaker job for the next day's evening match with Southend.
Once again, things started well for Pompey as Andy Barcham rifled the Blues into the lead after just two minutes. Things got even better in the second half as Cauley Woodrow was sent off for an elbow on Jed Wallace with the home side looking comfortable.
But Awford's task was made all too clear when his team capitulated against ten men with Will Atkinson and Barry Corr's goals turning the game on its head. There was to be no response from Pompey who slid to a fifth straight defeat.
The rumour will was already turning when it came to the subject of the next Portsmouth manager and speculation was rife when Crawley manager Richie Barker was sacked and his previous connections to C.E.O Mark Catlin were highlighted.
Other candidates included Oxford boss Chris Wilder who would go on to revive Northampton instead, Exeter manager Paul Tisdale and David Connolly amongst others.
For the time being, it was up to Andy Awford to arrest Pompey's slide and he did that thanks to a boring goalless draw at Hartlepool. The match was so bland that the highlights below contain the half-time whistle and the second half kick-off! The match may have been uninspiring but it stopped the rot.
Portsmouth ended the month in 17th position in League Two with 21 points from 18 games. Whoever Whittingham's replacement was going to be, he was sure to have a tough job on his hands...