After the wonder years of the 30's - early 50's, the late 50's to the early 60's were Pompey's darkness years, they lost their top flight status at the end of the 1958/1959 season, money soon became less and less partly leading to their relegation to the third division in the 1960/1961 season, although Pompey bounced back as Division Three champions the following year.
The clubs longest serving and most capped player Jimmy Dickinson finally retired in april 1965, with Pompey hanging on to their second division status on goal average. Also in this year Pompey as part of a cost saving measure scrapped their youth and reserve team a decision not reversed until 1972/1973. Pompey were largely anonomous in the second division until the early 70's, until John Deacon taking over as chairman in 1973, a new manager followed in the form of John Mortimore. Deacon provided money to break the transfer record twice in 1973, first in May with the purchase of Peter Marinello from Arsenal for £100,000, then in December buying Paul Went from Fulham for £155,000. Although his cash injection didnt really improve the on-pitch fortunes of Pompey. John Mortimore didnt last long being sacked in September 1974, with Ian St John replacing him. Unable to sustain the level of investment Pompey were in trouble again getting relegated to division three at the end of the 1975/1976 season.
The end of our club?
In November 1976 the club was in dire need of money, needing to raise £25,000 to stave off bankruptcy, Portsmouth's local paper The News led the SOS Pompey campaign to help save the club, with the supporters raising the money, and saving the club from bankruptcy. Portsmouth's money trouble was affecting the squad, players having to be sold off to raise money, leaving little or no money for replacements, so Pompey relied on young inexperienced players, this lead the club to be relegated to division four at the end of the 1977/1978 season with manager Ian St John being sacked in May, and Pompey legend Jimmy Dickinson taking the managers position.
Pompey recieved £100,000 from Brighton for Steve Foster in 1979 a record at the time, Pompey legend Jimmy Dickinson resigned from the managers job in June 1979 due to ill health, being replaced by Frank Burrows, the 1979-1980 season saw Pompey get promoted back to division three on goal difference.
Burrows was eventually sacked in March 1982 being replaced with Bobby Campbell. The lower half of the football league was finally left in the 1982/1983 season with Pompey becoming champions of the third divsion
The light at the end of the tunnel?
Pompey broke the bank again in 1983 signing Mark Hateley splashing £190,000. Bobby Campbell's reign of Pompey manager ended in May 1984 after being sacked, being replaced by Alan Ball, later this year Mark Hateley left Pompey to AC Milan for a club record fee of £1million. Pompey narrowly missed out on promotion to division one by goal difference at end of the 1984/1985 season.