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| Season 1987-88 |
| Pompey Appearances : Adrian Whitbread |
| Season: 1999/00 |
| League: Division One |
| Select and click opposing team for match details |
| Match Date | Fixture | Opponent | Result | Score |
| Sat 21 Aug 1999 | H | Stockport County | W | 2 - 0 |
| Sat 28 Aug 1999 | A | Barnsley | L | 0 - 6 |
| Mon 30 Aug 1999 | H | Huddersfield Town | D | 0 - 0 |
| Sat 11 Sep 1999 | H | Ipswich Town | D | 1 - 1 |
| Sat 2 Oct 1999 | A | Crystal Palace | L | 0 - 4 |
| Sat 16 Oct 1999 | H | Charlton Athletic | L | 0 - 2 |
| Tue 19 Oct 1999 | H | Walsall | W | 5 - 1 |
| Sat 23 Oct 1999 | A | Queens Park Rangers | D | 0 - 0 |
| Tue 26 Oct 1999 | A | Grimsby Town | L | 0 - 1 |
| Sat 30 Oct 1999 | H | Crystal Palace | W | 3 - 1 |
| Wed 3 Nov 1999 | A | Manchester City | L | 2 - 4 |
| Sat 6 Nov 1999 | H | Birmingham City | D | 2 - 2 |
| Tue 9 Nov 1999 | A | Fulham | L | 0 - 1 |
| Sat 20 Nov 1999 | H | Crewe Alexandra | L | 0 - 2 |
| Wed 24 Nov 1999 | A | Nottingham Forest | L | 0 - 2 |
| Sat 27 Nov 1999 | H | Bolton Wanderers | D | 0 - 0 |
| Sat 4 Dec 1999 | A | Sheffield Utd | L | 0 - 1 |
| Sat 18 Dec 1999 | H | Port Vale | D | 0 - 0 |
| Sun 26 Dec 1999 | A | Swindon Town | D | 1 - 1 |
| Tue 28 Dec 1999 | H | Blackburn Rovers | L | 1 - 2 |
| Mon 3 Jan 2000 | A | Norwich City | L | 1 - 2 |
| Sat 15 Jan 2000 | H | Wolverhampton Wanderers | L | 2 - 3 |
| Sat 22 Jan 2000 | A | Stockport County | D | 1 - 1 |
| Sat 29 Jan 2000 | H | Barnsley | W | 3 - 0 |
| Sat 5 Feb 2000 | A | Huddersfield Town | W | 1 - 0 |
| Sat 12 Feb 2000 | H | Fulham | L | 0 - 1 |
| Tue 22 Feb 2000 | A | Bolton Wanderers | L | 0 - 3 |
| Wed 1 Mar 2000 | H | Tranmere Rovers | L | 1 - 2 |
| Sat 4 Mar 2000 | A | Ipswich Town | W | 1 - 0 |
| Tue 7 Mar 2000 | A | Birmingham City | L | 0 - 1 |
| Sat 11 Mar 2000 | H | Nottingham Forest | W | 2 - 1 |
| Sat 18 Mar 2000 | A | Crewe Alexandra | W | 3 - 1 |
| Tue 21 Mar 2000 | H | West Bromwich Albion | W | 2 - 0 |
| Sat 25 Mar 2000 | H | Swindon Town | W | 4 - 1 |
| Sat 1 Apr 2000 | A | Port Vale | L | 0 - 2 |
| Sat 8 Apr 2000 | H | Norwich City | W | 2 - 1 |
| Fri 21 Apr 2000 | A | Charlton Athletic | D | 1 - 1 |
| Sat 29 Apr 2000 | A | Walsall | L | 0 - 1 |
| Sun 7 May 2000 | H | Queens Park Rangers | L | 1 - 3 |
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