Sat 23 Jan 1999
FA Cup Round 4
Pompey 1 Leeds United 5
| Pos | Player | Goals | Subs |
| 1 | Alan Knight | ||
| 2 | Matthew Robinson | ||
| 3 | Fitzroy Simpson | ||
| 4 | Alan McLoughlin | ||
| 5 | Adrian Whitbread | ||
| 6 | David Waterman | * | |
| 6 | Martin Phillips | s | |
| 7 | Luke Nightingale | 1 | * |
| 7 | Thomas Thogersen | s | |
| 8 | Jeff Peron | ||
| 9 | Michalis Vlachos | ||
| 10 | Steve Claridge | ||
| 11 | Sammy Igoe |
| Select Pompey player for stats |
| Scorers: Nightingale Manager: Alan Ball Attendance: 18,864 |
Season 1998/99
Fixtures
Select opponent for Pompey line-up Change Season
| Date | Opponent | Result | Score |
| Sat 8 Aug 1998 | Watford H | L | 1 - 2 |
| Tue 11 Aug 1998 | Plymouth Argyle- Football League Cup Round 1 1st Leg A | W | 3 - 1 |
| Sat 15 Aug 1998 | Tranmere Rovers A | D | 1 - 1 |
| Tue 18 Aug 1998 | Plymouth Argyle- Football League Cup Round 1 2nd Leg H | W | 3 - 2 |
| Sat 22 Aug 1998 | Ipswich Town H | D | 0 - 0 |
| Sat 29 Aug 1998 | Huddersfield Town A | D | 3 - 3 |
| Mon 31 Aug 1998 | Queens Park Rangers H | W | 3 - 0 |
| Sun 6 Sep 1998 | Oxford United A | L | 0 - 3 |
| Tue 8 Sep 1998 | Bury A | L | 1 - 2 |
| Sat 12 Sep 1998 | Swindon Town H | W | 5 - 2 |
| Tue 15 Sep 1998 | Wimbledon- Football League Cup Round 2 1st Leg H | W | 2 - 1 |
| Sat 19 Sep 1998 | Port Vale A | W | 2 - 0 |
| Tue 22 Sep 1998 | Wimbledon- Football League Cup Round 2 2nd Leg A | L | 1 - 4 |
| Sat 26 Sep 1998 | Sunderland H | D | 1 - 1 |
| Tue 29 Sep 1998 | Birmingham City H | L | 0 - 1 |
| Sat 3 Oct 1998 | Sheffield United A | L | 1 - 2 |
| Sat 10 Oct 1998 | Bristol City A | D | 2 - 2 |
| Sat 17 Oct 1998 | Wolverhampton Wanderers H | W | 1 - 0 |
| Tue 20 Oct 1998 | Bradford City H | L | 2 - 4 |
| Sat 24 Oct 1998 | Barnsley A | L | 1 - 2 |
| Sat 7 Nov 1998 | Crystal Palace A | L | 1 - 4 |
| Tue 10 Nov 1998 | Norwich City H | L | 1 - 2 |
| Sat 14 Nov 1998 | Grimsby Town A | D | 1 - 1 |
| Sat 21 Nov 1998 | West Bromwich Albion H | W | 2 - 1 |
| Sat 28 Nov 1998 | Stockport County A | L | 0 - 2 |
| Sat 5 Dec 1998 | Crewe Alexandra H | W | 2 - 0 |
| Sun 13 Dec 1998 | Grimsby Town H | L | 0 - 1 |
| Sat 19 Dec 1998 | Bolton Wanderers A | L | 1 - 3 |
| Sat 26 Dec 1998 | Ipswich Town A | L | 0 - 3 |
| Mon 28 Dec 1998 | Oxford United H | D | 2 - 2 |
| Sat 2 Jan 1999 | Nottingham Forest- FA Cup Round 3 A | W | 1 - 0 |
| Sat 9 Jan 1999 | Watford A | D | 0 - 0 |
| Sat 16 Jan 1999 | Huddersfield Town H | W | 1 - 0 |
| Sat 23 Jan 1999 | Leeds United- FA Cup Round 4 H | L | 1 - 5 |
| Sat 30 Jan 1999 | Queens Park Rangers A | D | 1 - 1 |
| Sat 6 Feb 1999 | Tranmere Rovers H | D | 1 - 1 |
| Sat 13 Feb 1999 | Bury H | W | 2 - 1 |
| Sat 20 Feb 1999 | Swindon Town A | D | 3 - 3 |
| Sat 27 Feb 1999 | Port Vale H | W | 4 - 0 |
| Tue 2 Mar 1999 | Sunderland A | L | 0 - 2 |
| Sat 6 Mar 1999 | Birmingham City A | L | 1 - 4 |
| Tue 9 Mar 1999 | Sheffield United H | W | 1 - 0 |
| Sat 13 Mar 1999 | Crystal Palace H | D | 1 - 1 |
| Sat 20 Mar 1999 | Norwich City A | D | 0 - 0 |
| Sun 28 Mar 1999 | Barnsley H | L | 1 - 3 |
| Sat 3 Apr 1999 | Wolverhampton Wanderers A | L | 0 - 2 |
| Mon 5 Apr 1999 | Bristol City H | L | 0 - 1 |
| Sat 10 Apr 1999 | Bradford City A | L | 1 - 2 |
| Sat 17 Apr 1999 | West Bromwich Albion A | D | 2 - 2 |
| Sat 24 Apr 1999 | Stockport County H | W | 3 - 1 |
| Sat 1 May 1999 | Crewe Alexandra A | L | 1 - 3 |
| Sun 9 May 1999 | Bolton Wanderers H | L | 0 - 2 |
