The Fratton Park club have twice entered administration in the past five years and tumbled down the football pyramid since winning the FA Cup in 2008 and reaching the final in 2010.
But since avoiding liquidation in 2013 and the Pompey Supporters' Trust seizing financial control of the club, their off-field fortunes have turned around and they can redirect their attention to matters on the pitch.
Five points from the past three games have seen Portsmouth climb to eighth in League Two and standing between them and a potential place in the top six on are York, who go into Saturday's without a win in four.
Before that, on Friday, leaders Burton Albion host Cambridge United while Dagenham and Redbridge could leapfrog 17th-placed Exeter City with a win at Victoria Road.
Burton replaced Bury in top spot at the weekend after David Flitcroft's men lost to Exeter, but they remain in the top three and can keep the pressure up if they stretch Tranmere Rovers' winless run to six.
New manager Keith Curle guided bottom club Carlisle United to their first victory in just his second game in charge at the weekend and they could climb out of the bottom two with three points at Hartlepool United.
Oxford United sit between those two clubs having already lost five times this season before hosting Newport County.
Second-placed Wycombe Wanderers have not lost in the league since August 19 and it is difficult to predict what type of test Northampton Town will provide - they sit fifth but have put back-to-back wins together just once so far this term.
Below Wanderers, four points separate Southend United and Morecambe in fourth and sixth position, respectively. They meet at Roots Hall with the hosts aiming for a first win in the ninth league clash between the clubs.
Plymouth Argyle will have to do without promising full-back Ben Purrington when they take on Shrewsbury Town – and for "a good few weeks" – after he broke his wrist in last week's defeat at Accrington Stanley.
That result made it back-to-back successes for Stanley following their incredible 5-4 triumph at Northampton the week before and they will have to continue that good form if they are to come away from their visit to Mansfield Town with any points.
Luton Town tied talented midfielder Matt Robinson to a new deal in the week and he will likely be in the side that travels to Stevenage on Saturday, with ambitions to force their way into top six.
Cheltenham sit one place above Luton and their primary concern will be limiting the service to seven-goal striker Matt Tubbs as AFC Wimbledon visit Whaddon Road.