| Club: | Portsmouth |
| Season: | 1998–99 |
| Manager: | Alan Ball |
| Chairman: | Martin Gregory (until 18 December) Les Parris (from 18 December - 18 May 1999) |
| Stadium: | Fratton Park |
| League: | Football League First Division |
| League Result: | 19th |
| Cup2: | FA Cup |
| Cup2 Result: | Fourth round |
| Cup3: | Worthington Cup |
| Cup3 Result: | Second round |
| League Topscorer: | Aloisi (14) |
| Season Topscorer: | Aloisi (17) |
| Highest Attendance: | 19,284 vs. Crewe Alexandra (5 December 1998) |
| Lowest Attendance: | 8,180 vs Grimsby Town (13 December 1998) |
| Average Attendance: | 13,732 |
| Prevseason: | 1997–98 |
| Nextseason: | 1999–2000 |
During the 1998–99 English football season, Portsmouth F.C. competed in the Football League First Division.
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[1] and in February 1999, Portsmouth went into receivership.[2] 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.[3]
See main article: 1998–99 Football League.
Portsmouth's score comes first[4]
| Win | Draw | Loss |
| Date | Opponent | Venue | Result | Attendance | Scorers | |
|---|---|---|---|---|---|---|
| 8 August 1998 | Watford | H | 1–2 | 15,275 | Aloisi | |
| 15 August 1998 | Tranmere Rovers | A | 1–1 | 6,714 | Aloisi | |
| 22 August 1998 | Ipswich Town | H | 0–0 | 12,002 | ||
| 29 August 1998 | Huddersfield Town | A | 3–3 | 10,085 | Aloisi (2), McLoughlin (pen) | |
| 31 August 1998 | Queens Park Rangers | H | 3–0 | 12,106 | Aloisi, McLoughlin, Phillips | |
| 6 September 1998 | Oxford United | A | 0–3 | 6,626 | ||
| 8 September 1998 | Bury | A | 1–2 | 4,310 | McLoughlin (pen) | |
| 12 September 1998 | Swindon Town | H | 5–2 | 10,105 | Aloisi (2), Igoe (2), Claridge | |
| 19 September 1998 | Port Vale | A | 2–0 | 5,992 | Aloisi, Durnin | |
| 26 September 1998 | Sunderland | H | 1–1 | 17,022 | Igoe | |
| 29 September 1998 | Birmingham City | H | 0–1 | 11,843 | ||
| 3 October 1998 | Sheffield United | A | 1–2 | 15,386 | Aloisi | |
| 10 October 1998 | Bristol City | A | 2–2 | 13,056 | Igoe, Claridge | |
| 17 October 1998 | Wolverhampton Wanderers | H | 1–0 | 13,681 | McLoughlin (pen) | |
| 20 October 1998 | Bradford City | H | 2–4 | 10,062 | Aloisi (2) | |
| 24 October 1998 | Barnsley | A | 1–2 | 15,152 | Durnin | |
| 7 November 1998 | Crystal Palace | A | 1–4 | 20,188 | Aloisi | |
| 10 November 1998 | Norwich City | H | 1–2 | 9,335 | Aloisi | |
| 14 November 1998 | Grimsby Town | A | 1–1 | 6,236 | Aloisi | |
| 21 November 1998 | West Bromwich Albion | H | 2–1 | 11,144 | Nightingale (2) | |
| 28 November 1998 | Stockport County | A | 0–2 | 7,504 | ||
| 5 December 1998 | Crewe Alexandra | H | 2–0 | 19,284 | McLoughlin, Claridge | |
| 13 December 1998 | Grimsby Town | H | 0–1 | 8,180 | ||
| 19 December 1998 | Bolton Wanderers | A | 1–3 | 15,981 | Igoe | |
| 26 December 1998 | Ipswich Town | A | 0–3 | 21,805 | ||
| 28 December 1998 | Oxford United | H | 2–2 | 12,604 | Claridge (2, 1 pen) | |
| 9 January 1999 | Watford | A | 0–0 | 12,057 | ||
| 16 January 1999 | Huddersfield Town | H | 1–0 | 10,334 | Claridge | |
| 30 January 1999 | Queens Park Rangers | A | 1–1 | 12,270 | Nightingale | |
| 6 February 1999 | Tranmere Rovers | H | 1–1 | 10,597 | Whittingham | |
| 13 February 1999 | Bury | H | 2–1 | 9,062 | Robinson, Whittingham | |
| 20 February 1999 | Swindon Town | A | 3–3 | 10,230 | Claridge (2), Péron | |
| 27 February 1999 | Port Vale | H | 4–0 | 12,838 | McLoughlin (pen), Whittingham (3) | |
| 2 March 1999 | Sunderland | A | 0–2 | 37,656 | ||
| 6 March 1999 | Birmingham City | A | 1–4 | 20,617 | Whittingham | |
| 9 March 1999 | Sheffield United | H | 1–0 | 10,287 | Awford | |
| 13 March 1999 | Crystal Palace | H | 1–1 | 15,120 | Whittingham | |
| 20 March 1999 | Norwich City | A | 0–0 | 16,662 | ||
| 28 March 1999 | Barnsley | H | 1–3 | 13,337 | Durnin | |
| 3 April 1999 | Wolverhampton Wanderers | A | 0–2 | 23,262 | ||
| 5 April 1999 | Bristol City | H | 0–1 | 13,026 | ||
| 10 April 1999 | Bradford City | A | 1–2 | 13,552 | Durnin | |
| 17 April 1999 | West Bromwich Albion | A | 2–2 | 12,750 | Durnin (2) | |
| 24 April 1999 | Stockport County | H | 3–1 | 11,212 | Claridge, Simpson, Durnin | |
| 1 May 1999 | Crewe Alexandra | A | 1–3 | 5,759 | McLoughlin | |
| 9 May 1999 | Bolton Wanderers | H | 0–2 | 16,015 |
See main article: 1998–99 FA Cup.
| R3 | 2 January 1999 | Nottingham Forest | A | 1–0 | 10,092 | Claridge | |
| R4 | 23 January 1999 | Leeds United | H | 1–5 | 18,864 | Nightingale |
See main article: 1998–99 Football League Cup.
| R1 1st Leg | 11 August 1998 | Plymouth Argyle | A | 3–1 | 4,380 | McLoughlin (pen), Vlachos, Aloisi | |
| R1 2nd Leg | 18 August 1998 | Plymouth Argyle | H | 3–2 (won 6–3 on agg) | 5,479 | Hillier, McLoughlin (pen), 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 (lost 3–5 on agg) | 3,756 | Whitbread |
Squad at end of season[5]