That’s if you look ahead to what lies in store for the Blues fixture-wise between now and the end of the year.
Indeed, if this season’s form guide is anything to go by, it could well turn out to be a prolonged winter of discontent rather than the joyous winter wonderland many fans would have been anticipating at Fratton Park when the season kicked off back in August.
The latest disappointment in a season already verging on a disaster occurred on Saturday at Bristol Rovers, where Pompey threw away a 2-0 lead with just 12 minutes remaining on the clock.
It was a second game in a row that a stoppage-time goal denied the Blues vital points, and the fourth time already this term that Kenny Jackett’s side conceded late on to ensure yet more misery.
And as the clocks went back just a few hours later, the unsuspecting draw also saw time expire on what was a critical period in Pompey’s season.
With games against clubs in and around the Blues in the League One table, the previous month’s fixtures were all deemed winnable ones – matches that would surely propel the team up the table.
However, 11 points from the 18 on offer has failed to see the Blues make significant gains on the division’s early pacesetters.
Instead, a league placing of 20th at the beginning of that six-game spell has been replaced with a 16th-place spot, with hard-fought wins against Bolton, Doncaster Rovers and Lincoln negated by a loss at Wimbledon and disappointing draws against Gillingham and Rovers.
At this moment there’s no evidence to suggest those disgruntled fans will get their wish.
But with Pompey set to embark on a League One time line that could prove treacherous even for a side bang in form, Jackett could be set for a career-defining sink or swim period in his Blues managerial reign.
The Fratton Park outfit have 10 league fixtures between now and the end of 2019.
Games against Southend (22nd), Rochdale (14th), Accrington (18th) and MK Dons (20th) should provide hope.
Yet the other six matches will prove a lot more difficult to negotiate – despite them all being at home.
Five of those games will be against teams currently in the top six (Ipswich, Wycombe, Peterborough, Fleetwood and Oxford), with the remaining one against a side relegated from the Championship last season – Rotherham.
On Saturday, the Blues kick off their run-in to the year’s end by hosting an Oxford United side sitting fifth in the table and unbeaten in their past eight league games.
Next up is a reunion with Sol Campbell and Southend, who have two wins in 19 matches all season, on Tuesday, November 5.
Then it's the visit of Joey Barton’s Fleetwood to PO4 (November 16) – a side currently sitting fourth in the standings with the third highest number of goals scored this term.
Following that is a trip to Rochdale (Nov 23), before Rotherham make the trip to the south coast on November 26.
Like the Blues, they’ve been under-performing this season but retain hope of making a return to the Championship at the first time of asking.
The first league game in December is a home tie against third-placed Peterborough on the 7th – the division’s top scorers and a side with only one defeat to their name since the second day of the season.
An away trip to Accrington follows on December 14 – then it’s the festive fixtures with games against Ipswich (December 21), Wycombe (26th) and MK Dons (29th) lying in wait.
At this moment in time, Pompey couldn’t have asked for more difficult fixtures either side of Christmas Day, with both Ipswich and Wycombe sitting first and second in the table respectively.
The Chairboys have, of course, already got one over Jackett’s side this term – last month’s 1-0 win at Adams Park.
That defeat witnessed the first visible signs of discontent among the Fratton faithful, with the travelling fans calling for the manager to be sacked.
If Jackett’s still at the helm for that Boxing Day visit, then it would suggest an upturn in fortunes had been achieved, with Pompey fans receiving the perfect Christmas present.
But bearing in mind what lies ahead between now and then – and let’s not forget there’s FA Cup progress to negotiate, too – that remains a huge ask.
Jackett could feasibly be the ghost of Christmas past come that stage, with the Blues searching for the promised land of the Championship with new wise man at the helm.