| Date | Home | Score | Away | R | Tournament |
|---|---|---|---|---|---|
| 28 Mar 1999 |
Portsmouth
|
1–3 |
|
A | ENG · Championship |
| 20 Mar 1999 |
Norwich City
|
0–0 |
|
D | ENG · Championship |
| 13 Mar 1999 |
Portsmouth
|
1–1 |
|
D | ENG · Championship |
| 09 Mar 1999 |
Portsmouth
|
1–0 |
|
H | ENG · Championship |
| 06 Mar 1999 |
Birmingham City
|
4–1 |
|
H | ENG · Championship |
| 02 Mar 1999 |
Sunderland
|
2–0 |
|
H | ENG · Championship |
| 27 Feb 1999 |
Portsmouth
|
4–0 |
|
H | ENG · Championship |
| 20 Feb 1999 |
Swindon Town
|
3–3 |
|
D | ENG · Championship |
| 13 Feb 1999 |
Portsmouth
|
2–1 |
|
H | ENG · Championship |
| 06 Feb 1999 |
Portsmouth
|
1–1 |
|
D | ENG · Championship |
| 30 Jan 1999 |
Queens Park Rangers
|
1–1 |
|
D | ENG · Championship |
| 23 Jan 1999 |
Portsmouth
|
1–5 |
|
A | ENG · FA Cup Round 4 |
| 16 Jan 1999 |
Portsmouth
|
1–0 |
|
H | ENG · Championship |
| 09 Jan 1999 |
Watford
|
0–0 |
|
D | ENG · Championship |
| 02 Jan 1999 |
Nottingham Forest
|
0–1 |
|
A | ENG · FA Cup Round 3 |
| 28 Dec 1998 |
Portsmouth
|
2–2 |
|
D | ENG · Championship |
| 26 Dec 1998 |
Ipswich Town
|
3–0 |
|
H | ENG · Championship |
| 19 Dec 1998 |
Bolton Wanderers
|
3–1 |
|
H | ENG · Championship |
| 13 Dec 1998 |
Portsmouth
|
0–1 |
|
A | ENG · Championship |
| 05 Dec 1998 |
Portsmouth
|
2–0 |
|
H | ENG · Championship |
| 28 Nov 1998 |
Stockport County
|
2–0 |
|
H | ENG · Championship |
| 21 Nov 1998 |
Portsmouth
|
2–1 |
|
H | ENG · Championship |
| 14 Nov 1998 |
Grimsby Town
|
1–1 |
|
D | ENG · Championship |
| 10 Nov 1998 |
Portsmouth
|
1–2 |
|
A | ENG · Championship |
| 07 Nov 1998 |
Crystal Palace
|
4–1 |
|
H | ENG · Championship |
| 24 Oct 1998 |
Barnsley
|
2–1 |
|
H | ENG · Championship |
| 20 Oct 1998 |
Portsmouth
|
2–4 |
|
A | ENG · Championship |
| 17 Oct 1998 |
Portsmouth
|
1–0 |
|
H | ENG · Championship |
| 10 Oct 1998 |
Bristol City
|
2–2 |
|
D | ENG · Championship |
| 03 Oct 1998 |
Sheffield United
|
2–1 |
|
H | ENG · Championship |
| 29 Sep 1998 |
Portsmouth
|
0–1 |
|
A | ENG · Championship |
| 26 Sep 1998 |
Portsmouth
|
1–1 |
|
D | ENG · Championship |
| 22 Sep 1998 | Wimbledon | 4–1 |
|
H | ENG · League Cup Round 2 · Leg 2 |
| 19 Sep 1998 |
Port Vale
|
0–2 |
|
A | ENG · Championship |
| 15 Sep 1998 |
Portsmouth
|
2–1 | Wimbledon | H | ENG · League Cup Round 2 · Leg 1 |
| 12 Sep 1998 |
Portsmouth
|
5–2 |
|
H | ENG · Championship |
| 08 Sep 1998 |
Bury
|
2–1 |
|
H | ENG · Championship |
| 06 Sep 1998 |
Oxford United
|
3–0 |
|
H | ENG · Championship |
| 31 Aug 1998 |
Portsmouth
|
3–0 |
|
H | ENG · Championship |
| 29 Aug 1998 |
Huddersfield Town
|
3–3 |
|
D | ENG · Championship |