| Club: | Portsmouth F.C. |
| Season: | 1999–2000 |
| Manager: | Alan Ball (until 9 December) Bob McNab (caretaker) Tony Pulis (from January) |
| Chairman: | Milan Mandarić |
| Stadium: | Fratton Park |
| League: | First Division |
| League Result: | 18th |
| Cup1: | FA Cup |
| Cup1 Result: | Third round |
| Cup2: | Worthington Cup |
| Cup2 Result: | Second round |
| League Topscorer: | Steve Claridge (14) |
| Season Topscorer: | Steve Claridge (14) |
| Highest Attendance: | 19,015 vs. Manchester City (24 April 2000) |
| Lowest Attendance: | 9,042 vs. Walsall (19 October 1999) |
| Average Attendance: | 14,028 |
| Prevseason: | 1998–99 |
| Nextseason: | 2000–01 |
During the 1999–2000 English football season, Portsmouth F.C. competed in the Football League First Division.[1]
Manager Alan Ball's contract was terminated on 9 December with Portsmouth in the relegation zone. He was replaced by Bristol City manager Tony Pulis, who steered the club to survival in the First Division.
The end of the season saw the retirement of club goalkeeping legend Alan Knight, who made 801 career appearances over 22 years, all spent at Fratton Park. His final appearance came in a First Division match against Norwich City at Carrow Road in January.
Portsmouth ended their kit manufacturing deal with Admiral after two years, to manufacture their own kits under the brand name "Pompey Sport".[2]
See main article: 1999–2000 Football League.
Portsmouth's score comes first
| Win | Draw | Loss |
| Date | Opponent | Venue | Result | Attendance | Scorers | |
|---|---|---|---|---|---|---|
| 7 August 1999 | Sheffield United | H | 2–0 | 17,667 | Miglioranzi, Whittingham | |
| 14 August 1999 | Wolverhampton Wanderers | A | 1–1 | 21,024 | Allen | |
| 21 August 1999 | Stockport County | H | 2–0 | 15,002 | Miglioranzi, Allen | |
| 28 August 1999 | Barnsley | A | 0–6 | 13,792 | ||
| 30 August 1999 | Huddersfield Town | H | 0–0 | 13,105 | ||
| 11 September 1999 | Ipswich Town | H | 1–1 | 16,304 | Whittingham | |
| 18 September 1999 | Tranmere Rovers | A | 4–2 | 5,870 | Péron (2), Whittingham, Vlachos | |
| 25 September 1999 | Grimsby Town | H | 1–2 | 12,073 | McLoughlin (pen) | |
| 2 October 1999 | Crystal Palace | A | 0–4 | 15,221 | ||
| 16 October 1999 | Charlton Athletic | H | 0–2 | 14,812 | ||
| 19 October 1999 | Walsall | H | 5–1 | 9,042 | Thøgersen (2), Bradbury, McLoughlin (2 pens) | |
| 23 October 1999 | Queens Park Rangers | A | 0–0 | 13,303 | ||
| 26 October 1999 | Grimsby Town | A | 0–1 | 5,912 | ||
| 30 October 1999 | Crystal Palace | H | 3–1 | 13,018 | Claridge (2), Bradbury | |
| 3 November 1999 | Manchester City | A | 2–4 | 31,660 | Bradbury, Thøgersen | |
| 6 November 1999 | Birmingham City | H | 2–2 | 12,756 | McLoughlin (2 pens) | |
| 9 November 1999 | Fulham | A | 0–1 | 13,229 | ||
| 14 November 1999 | West Bromwich Albion | A | 2–3 | 11,483 | Whittingham, Awford | |
| 20 November 1999 | Crewe Alexandra | H | 0–2 | 11,550 | ||
| 24 November 1999 | Nottingham Forest | A | 0–2 | 13,841 | ||
| 27 November 1999 | Bolton Wanderers | H | 0–0 | 10,431 | ||
| 4 December 1999 | Sheffield United | A | 0–1 | 10,834 | ||
| 18 December 1999 | Port Vale | H | 0–0 | 11,869 | ||
| 26 December 1999 | Swindon Town | A | 1–1 | 10,279 | Claridge | |
| 28 December 1999 | Blackburn Rovers | H | 1–2 | 15,208 | Claridge | |
| 3 January 2000 | Norwich City | A | 1–2 | 16,637 | Bradbury | |
| 15 January 2000 | Wolverhampton Wanderers | H | 2–3 | 13,255 | Igoe, Claridge | |
| 22 January 2000 | Stockport County | A | 1–1 | 8,008 | Hughes | |
| 29 January 2000 | Barnsley | H | 3–0 | 12,201 | Claridge (3) | |
| 5 February 2000 | Huddersfield Town | A | 1–0 | 12,753 | Claridge | |
| 12 February 2000 | Fulham | H | 0–1 | 17,337 | ||
| 22 February 2000 | Bolton Wanderers | A | 0–3 | 12,672 | ||
| 1 March 2000 | Tranmere Rovers | H | 1–2 | 10,759 | Claridge (pen) | |
| 4 March 2000 | Ipswich Town | A | 1–0 | 20,305 | Claridge | |
| 7 March 2000 | Birmingham City | A | 0–1 | 19,573 | ||
| 11 March 2000 | Nottingham Forest | H | 2–1 | 14,336 | Thøgersen, Claridge | |
| 18 March 2000 | Crewe Alexandra | A | 3–1 | 6,188 | Claridge, Thøgersen, Harper | |
| 21 March 2000 | West Bromwich Albion | H | 2–0 | 14,760 | Claridge (pen), Derry | |
| 25 March 2000 | Swindon Town | H | 4–1 | 15,305 | Whitbread, Bradbury (3) | |
| 1 April 2000 | Port Vale | A | 0–2 | 5,426 | ||
| 8 April 2000 | Norwich City | H | 2–1 | 14,003 | Harper, Moore | |
| 15 April 2000 | Blackburn Rovers | A | 1–1 | 19,263 | Hughes | |
| 21 April 2000 | Charlton Athletic | A | 1–1 | 20,043 | Bradbury | |
| 24 April 2000 | Manchester City | H | 2–2 | 19,015 | Bradbury (2, 1 pen) | |
| 29 April 2000 | Walsall | A | 0–1 | 8,151 | ||
| 7 May 2000 | Queens Park Rangers | H | 1–3 | 16,301 | Allen |
See main article: 1999–2000 FA Cup.
| R3 | 11 December 1999 | Sunderland | A | 0–1 | 26,535 |
See main article: 1999–2000 Football League Cup.
| R1 1st Leg | 17 August 1999 | Torquay United | A | 0–0 | 3,209 | ||
| R1 2nd Leg | 24 August 1999 | Torquay United | H | 3–0 | 8,741 | Nightingale (2), Lovell | |
| R2 1st Leg | 14 September 1999 | Blackburn Rovers | H | 0–3 | 8,542 | ||
| R2 2nd Leg | 22 September 1999 | Blackburn Rovers | A | 1–3 | 7,512 | McLoughlin |