Kenny Jackett and his team will be looking to avoid a rewrite of the Pompey history books tonight.
The Blues travel to The Valley to take on Charlton in the much-maligned Checkatrade Trophy (7.45pm).
Saturday’s FA Cup exit at the hands of Luton ensured Pompey go into the game on the back of four straight losses.
But not since the 2013-14 season have Blues fans experienced five consecutive defeats.
That unfortunate run of results came in the November of that season and ultimately cost Guy Whittingham his job as Pompey manager.
No-one is saying a similar fate awaits Jackett if Charlton condemn Pompey to five straight losses tonight.
The Blues, who are in transition, are still finding their feet in League One and have enjoyed some good results this term under new ownership.
But with Pompey experiencing forward momentum in recent years, such a run of results is something not used to at Fratton Park in recent times.
In November 2013, four of those reverses came under Whittingham’s stewardship - Stevenage (FA Cup), Newport (JP Trophy), Wimbledon and Scunthorpe (both league) – with caretaker boss Andy Awford following that up by losing his first game in charge against Southend, before temporarily reversing the trend with draws against Hartlepool and Wycombe.
The season before represents the only other campaign in the past 10 when five or more consecutive defeats have been recorded by the Blues.
However, that happened twice during that 2012-13 League One term, as Pompey’s very existence lay in the balance.
Seven in a row were registered between October 23, 2012, and November 7 of that year, with Michael Appleton at the helm for four of those games.
Caretaker boss Whittingham was in charge for the other three, before he had to watch from the sidelines as Pompey suffered nine defeats in succession between December 26 and February 9, 2013, as the club accepted relegation to the bottom tier of the Football League was inevitable.
Prior that, only three other seasons in the past 10 witnessed four defeats in a row.
In the 2010-11 Championship campaign, Steve Cotterill oversaw defeats to Watford, Hull and Nottingham Forest, plus an FA Cup third-round exit at the hands of Brighton.
The Blues’ last season in the Premier League saw the team experience three defeats in a row on three separate occasions.
But four in a row where registered between November 7, 2009 and December 1, 2009, which contributed to Paul Hart losing his job.
Although, caretaker bosses Ian Woan and Paul Groves took charge of the fourth of those – a 4-2 Capital One Cup defeat at the hands of Aston Villa.
The same consequences were experienced by Tony Adams just seven months previous.
Despite leading twice against Liverpool, a 3-2 February 2009 defeat at home to the Reds was his fourth in a row and saw him sacked.