Tony Adams failed, Paul Hart didn’t succeed and Avram Grant was found wanting.
But last night, Steve Cotterill achieved what his many predecessors had not – and emulated Harry Redknapp.
Not since October 2008 had a Blues side won successive league games.
On that occasion, the man whose name these days is rarely uttered in these parts oversaw victories over Spurs and Stoke.
Since then – absolutely nothing.
That all changed with a 3-1 triumph over Bristol City in the famous old surrounds of Fratton Park last night.
On the face of it, back-to-back league wins should attract nothing more than a polite ripple of applause rather than a standing ovation.
But considering Pompey’s demise over that same period, it represents progress.
And that is all the tangible proof fans need as their club attempt to scramble from the ashes of administration.
A week ago, Cotterill’s men were out of the Carling Cup and propping up the Championship with no wins from their opening seven games.
Suddenly, two victories in four days and the belief has come flooding back among the Fratton faithful.
What’s more, his troops have done it in eye-catching style.
The team that couldn’t score have now netted nine in their past two matches, conceding two in the process.
Even Hayden Mullins has started to score, while Aaron Mokoena finally has his first league goal in England after five-and-half years of trying.
As for John Utaka, the warm applause he received after being substituted is testament to the way he is beginning to turn around his previously-wilting reputation.
Last night, all were among the goals as Pompey’s fourth manager since Redknapp finally reaped a consecutive league victory.
The achievement was clinched during a second half which could well have yielded the opposite.
Jamie Ashdown had already come to the rescue several times, while at the other end, Dave Kitson and Mullins contrived to miss.
David James himself could only stand back, admire and applaud in the 40th minute when Jon Stead’s curling shot was somehow finger tipped around the post.
It was a moment of quality which even drew a rendition of ‘England’s number one’ from the Fratton end.
Fortunately for the hosts, the 29-year-old maintained that form after the break in what developed into a swashbuckling game of football.
Ashdown spent a soul-destroying four seasons as the understudy to James, while some sections of fans continue to doubt his worth.
Yesterday – with his former goalkeeping brother at the other end of the pitch – Pompey’s undisputed number one pulled off several superb stops.
And in the end that input proved to be priceless as the Blues took another sizeable stride towards the light.
Of course, Ashdown isn’t the only player rejuvenated under Cotterill these days.
Take a look at Utaka, who continued his rehabilitation with a magnificent opener on 51 minutes.
By that stage, Mullins had already contrived to head Liam Lawrence’s delightful cross into the ground before the ball was swatted over the bar by veteran James.
Meanwhile, Kitson had pounced on James failing to hold on to Nugent’s vicious half volley, only to half volley wide from eight yards out.
Then it was Utaka’s turn, the Nigerian cutting in from the left, carving a way across the area before crashing an unstoppable right-foot effort.
Cotterill has often spoken of using an arm around the shoulder technique on the complex Nigerian whose Pompey career has flattered to deceive.
Now there are encouraging signs it is working, even if he still isn’t operating in his favoured central-striking role.
Still, it was a lead that was to last just two minutes as Stead equalised, converting from close range.
Ashdown then saved from both Cole Skuse and Stead as City looked to take the lead for the first time in the encounter.
Then, on 58 minutes, Lawrence’s corner from the left was powerfully headed home at the near post by Mokoena.
James, who received a standing ovation around the ground when he made his way to the goal in the second half, had no chance – although he did thwart Kitson with a smart stop after the Pompey striker has carved a way through the defence.
At the other end, Keith Millen’s men should have levelled when the impressive Albert Adomah crossed from the right, only for substitute Danny Haynes to inexplicably head over. The Blues’ response was swift, Michael Brown winning the ball in the middle of the park and Lawrence feeding substitute Kanu.
The veteran striker simply slotted a pass across the goal for Mullins to gleefully rifle home.
Another Fratton Park match and another win, with Middlesbrough next on the horizon on Saturday.
A hat-trick of successive league wins?
After the past five days, it would take a brave person to rule out the thrilling possibility.