1998–99 Portsmouth F.C. season
During the 1998–99 English football season, Portsmouth F.C. competed in the Football League First Division.
Season summary
Portsmouth's centenary season, 1998–99, saw a serious financial crisis hit the club and in December 1998, chairman Martin Gregory quit his post after being targeted of abuse from Portsmouth fans which gave him no choice but to sell his 97% ownership of the club and in February 1999, Portsmouth went into receivership. They avoided relegation again that season, and were then saved from closure by new chairman Milan Mandarić, who saved the club with a takeover deal in May 1999. The new chairman immediately started investing.Final league table
Results
Portsmouth's score comes firstLegend
Football League First Division
FA Cup
| Round | Date | Opponent | Venue | Result | Attendance | Goalscorers |
| R3 | 2 January 1999 | Nottingham Forest | A | 1-0 | 10,092 | Claridge |
| R4 | 23 January 1999 | Leeds United | H | 1-5 | 18,864 | Nightingale |
League Cup
| Round | Date | Opponent | Venue | Result | Attendance | Goalscorers |
| R1 1st Leg | 11 August 1998 | Plymouth Argyle | A | 3-1 | 4,380 | McLoughlin, Vlachos, Aloisi |
| R1 2nd Leg | 18 August 1998 | Plymouth Argyle | H | 3-2 | 5,479 | Hillier, McLoughlin, Aloisi |
| R2 1st Leg | 15 September 1998 | Wimbledon | H | 2-1 | 7,010 | Aloisi, McLoughlin |
| R2 2nd Leg | 22 September 1998 | Wimbledon | A | 1-4 | 3,756 | Whitbread |