Mon 30 Aug 1999
Division One
Pompey 0 Huddersfield Town 0
| Pos | Player | Goals | Subs |
| 1 | Andy Petterson | ||
| 2 | Matthew Robinson | ||
| 3 | Fitzroy Simpson | ||
| 4 | Alan McLoughlin | ||
| 5 | Adrian Whitbread | ||
| 6 | Jason Cundy | ||
| 7 | Thomas Thogersen | ||
| 8 | Stefani Miglioranzi | * | |
| 8 | Adam Newton | s | |
| 9 | Rory Allen | ||
| 10 | Guy Whittingham | * | |
| 10 | Luke Nightingale | s | |
| 11 | Jeff Peron |
| Select Pompey player for stats |
| Scorers: Manager: Alan Ball Attendance: 13,105 |
Season 1999/00
Fixtures
Select opponent for Pompey line-up Change Season
| Date | Opponent | Result | Score |
| Sat 7 Aug 1999 | Sheffield United H | W | 2 - 0 |
| Sat 14 Aug 1999 | Wolverhampton Wanderers A | D | 1 - 1 |
| Tue 17 Aug 1999 | Torquay United- Football League Cup Round 2 1st Leg A | D | 0 - 0 |
| Sat 21 Aug 1999 | Stockport County H | W | 2 - 0 |
| Tue 24 Aug 1999 | Torquay United- Football League Cup Round 2 2nd Leg H | W | 3 - 0 |
| Sat 28 Aug 1999 | Barnsley A | L | 0 - 6 |
| Mon 30 Aug 1999 | Huddersfield Town H | D | 0 - 0 |
| Sat 11 Sep 1999 | Ipswich Town H | D | 1 - 1 |
| Tue 14 Sep 1999 | Blackburn Rovers- Football League Cup Round 2 1st Leg H | L | 0 - 3 |
| Sat 18 Sep 1999 | Tranmere Rovers A | W | 4 - 2 |
| Wed 22 Sep 1999 | Blackburn Rovers- Football League Cup Round 2 2nd Leg A | L | 1 - 3 |
| Sat 25 Sep 1999 | Grimsby Town H | L | 1 - 2 |
| Sat 2 Oct 1999 | Crystal Palace A | L | 0 - 4 |
| Sat 16 Oct 1999 | Charlton Athletic H | L | 0 - 2 |
| Tue 19 Oct 1999 | Walsall H | W | 5 - 1 |
| Sat 23 Oct 1999 | Queens Park Rangers A | D | 0 - 0 |
| Tue 26 Oct 1999 | Grimsby Town A | L | 0 - 1 |
| Sat 30 Oct 1999 | Crystal Palace H | W | 3 - 1 |
| Wed 3 Nov 1999 | Manchester City A | L | 2 - 4 |
| Sat 6 Nov 1999 | Birmingham City H | D | 2 - 2 |
| Tue 9 Nov 1999 | Fulham A | L | 0 - 1 |
| Sun 14 Nov 1999 | West Bromwich Albion A | L | 2 - 3 |
| Sat 20 Nov 1999 | Crewe Alexandra H | L | 0 - 2 |
| Wed 24 Nov 1999 | Nottingham Forest A | L | 0 - 2 |
| Sat 27 Nov 1999 | Bolton Wanderers H | D | 0 - 0 |
| Sat 4 Dec 1999 | Sheffield United A | L | 0 - 1 |
| Sat 11 Dec 1999 | Sunderland- FA Cup Round 3 A | L | 0 - 1 |
| Sat 18 Dec 1999 | Port Vale H | D | 0 - 0 |
| Sun 26 Dec 1999 | Swindon Town A | D | 1 - 1 |
| Tue 28 Dec 1999 | Blackburn Rovers H | L | 1 - 2 |
| Mon 3 Jan 2000 | Norwich City A | L | 1 - 2 |
| Sat 15 Jan 2000 | Wolverhampton Wanderers H | L | 2 - 3 |
| Sat 22 Jan 2000 | Stockport County A | D | 1 - 1 |
| Sat 29 Jan 2000 | Barnsley H | W | 3 - 0 |
| Sat 5 Feb 2000 | Huddersfield Town A | W | 1 - 0 |
| Sat 12 Feb 2000 | Fulham H | L | 0 - 1 |
| Tue 22 Feb 2000 | Bolton Wanderers A | L | 0 - 3 |
| Wed 1 Mar 2000 | Tranmere Rovers H | L | 1 - 2 |
| Sat 4 Mar 2000 | Ipswich Town A | W | 1 - 0 |
| Tue 7 Mar 2000 | Birmingham City A | L | 0 - 1 |
| Sat 11 Mar 2000 | Nottingham Forest H | W | 2 - 1 |
| Sat 18 Mar 2000 | Crewe Alexandra A | W | 3 - 1 |
| Tue 21 Mar 2000 | West Bromwich Albion H | W | 2 - 0 |
| Sat 25 Mar 2000 | Swindon Town H | W | 4 - 1 |
| Sat 1 Apr 2000 | Port Vale A | L | 0 - 2 |
| Sat 8 Apr 2000 | Norwich City H | W | 2 - 1 |
| Sat 15 Apr 2000 | Blackburn Rovers A | D | 1 - 1 |
| Fri 21 Apr 2000 | Charlton Athletic A | D | 1 - 1 |
| Mon 24 Apr 2000 | Manchester City H | D | 2 - 2 |
| Sat 29 Apr 2000 | Walsall A | L | 0 - 1 |
| Sun 7 May 2000 | Queens Park Rangers H | L | 1 - 3 |
