On June 7, 1989, Pompey signed Guy Whittingham, who would go on to become a Fratton Park legend.
The Blues had been in contact with the front man for a month before his move, trying to convince him to buy his way out of the army and make the step to becoming a professional footballer.
The club repaid Whttingham’s debt of £450 which turned out to be one of the bargains of the decade.
He went on to score 99 goals in the league and 112 in all competitions for the club during three spells at Fratton Park.
After returning to the club once more in a coaching capacity, Whittingham was named caretaker manager in 2011 and again in 2012 following the departures of Steve Cotterill and Michael Appleton respectively.
Whittingham was eventually named manager on a full-time basis but was relieved of his duties in November 2013.