After 'chasing the dream' earned the club a place in two FA Cup finals, relegation and financial struggles have taken their toll & Pompey's monetary position has become more severe
Pompey face a winding-up hearing next week over an unpaid tax bill and have not been able to pay their players or staff for January.
Peter Kubik, of the club's financial advisors UHY Hacker Young, told Press Association Sport: "They are in the process of seeking an administration order - an application to court seeking administration is due to go in any day.
"The club's bank accounts have been frozen due to the winding up hearing and they are finding it very difficult to trade. Once the administration order is in place the bank accounts will be made accessible again.
"We are aware that administration carries an automatic 10-point deduction by the Football League."
In February 2010 Portsmouth became the first Premier League club to enter administration and were deducted nine points, condemning them to relegation.
In November, Portsmouth's parent company, Convers Sports Initiatives (CSI) went into administration.
The tax bill is for between £900k and £1.2m but Kubik said there were many other outstanding bills to pay. Among these, the club needs to pay their electricity supplier in order to avoid being cut off.
"There are lots of bills they need to pay," added Kubik.
Currently lying in 17th place in the Championship table, a 10-point deduction from the Football League would put the South Coast club on 25 points, outside the relegation places only on goal difference.