| 22 Jan 2000 |
Stockport County
|
1–1
|
Portsmouth
|
D
|
ENG · Championship
|
| 15 Jan 2000 |
Portsmouth
|
2–3
|
Wolverhampton Wanderers
|
A
|
ENG · Championship
|
| 03 Jan 2000 |
Norwich City
|
2–1
|
Portsmouth
|
H
|
ENG · Championship
|
| 28 Dec 1999 |
Portsmouth
|
1–2
|
Blackburn Rovers
|
A
|
ENG · Championship
|
| 26 Dec 1999 |
Swindon Town
|
1–1
|
Portsmouth
|
D
|
ENG · Championship
|
| 18 Dec 1999 |
Portsmouth
|
0–0
|
Port Vale
|
D
|
ENG · Championship
|
| 11 Dec 1999 |
Sunderland
|
1–0
|
Portsmouth
|
H
|
ENG · FA Cup
Round 3
|
| 04 Dec 1999 |
Sheffield United
|
1–0
|
Portsmouth
|
H
|
ENG · Championship
|
| 27 Nov 1999 |
Portsmouth
|
0–0
|
Bolton Wanderers
|
D
|
ENG · Championship
|
| 24 Nov 1999 |
Nottingham Forest
|
2–0
|
Portsmouth
|
H
|
ENG · Championship
|
| 20 Nov 1999 |
Portsmouth
|
0–2
|
Crewe Alexandra
|
A
|
ENG · Championship
|
| 14 Nov 1999 |
West Bromwich Albion
|
3–2
|
Portsmouth
|
H
|
ENG · Championship
|
| 09 Nov 1999 |
Fulham
|
1–0
|
Portsmouth
|
H
|
ENG · Championship
|
| 06 Nov 1999 |
Portsmouth
|
2–2
|
Birmingham City
|
D
|
ENG · Championship
|
| 03 Nov 1999 |
Manchester City
|
4–2
|
Portsmouth
|
H
|
ENG · Championship
|
| 30 Oct 1999 |
Portsmouth
|
3–1
|
Crystal Palace
|
H
|
ENG · Championship
|
| 26 Oct 1999 |
Grimsby Town
|
1–0
|
Portsmouth
|
H
|
ENG · Championship
|
| 23 Oct 1999 |
Queens Park Rangers
|
0–0
|
Portsmouth
|
D
|
ENG · Championship
|
| 19 Oct 1999 |
Portsmouth
|
5–1
|
Walsall
|
H
|
ENG · Championship
|
| 16 Oct 1999 |
Portsmouth
|
0–2
|
Charlton Athletic
|
A
|
ENG · Championship
|
| 02 Oct 1999 |
Crystal Palace
|
4–0
|
Portsmouth
|
H
|
ENG · Championship
|
| 25 Sep 1999 |
Portsmouth
|
1–2
|
Grimsby Town
|
A
|
ENG · Championship
|
| 22 Sep 1999 |
Blackburn Rovers
|
3–1
|
Portsmouth
|
H
|
ENG · League Cup
Round 2 · Leg 2
|
| 18 Sep 1999 |
Tranmere Rovers
|
2–4
|
Portsmouth
|
A
|
ENG · Championship
|
| 14 Sep 1999 |
Portsmouth
|
0–3
|
Blackburn Rovers
|
A
|
ENG · League Cup
Round 2 · Leg 1
|
| 11 Sep 1999 |
Portsmouth
|
1–1
|
Ipswich Town
|
D
|
ENG · Championship
|
| 30 Aug 1999 |
Portsmouth
|
0–0
|
Huddersfield Town
|
D
|
ENG · Championship
|
| 28 Aug 1999 |
Barnsley
|
6–0
|
Portsmouth
|
H
|
ENG · Championship
|
| 24 Aug 1999 |
Portsmouth
|
3–0
|
Torquay United
|
H
|
ENG · League Cup
Round 1 · Leg 2
|
| 21 Aug 1999 |
Portsmouth
|
2–0
|
Stockport County
|
H
|
ENG · Championship
|
| 17 Aug 1999 |
Torquay United
|
0–0
|
Portsmouth
|
D
|
ENG · League Cup
Round 1 · Leg 1
|
| 14 Aug 1999 |
Wolverhampton Wanderers
|
1–1
|
Portsmouth
|
D
|
ENG · Championship
|
| 07 Aug 1999 |
Portsmouth
|
2–0
|
Sheffield United
|
H
|
ENG · Championship
|
| 09 May 1999 |
Portsmouth
|
0–2
|
Bolton Wanderers
|
A
|
ENG · Championship
|
| 01 May 1999 |
Crewe Alexandra
|
3–1
|
Portsmouth
|
H
|
ENG · Championship
|
| 24 Apr 1999 |
Portsmouth
|
3–1
|
Stockport County
|
H
|
ENG · Championship
|
| 17 Apr 1999 |
West Bromwich Albion
|
2–2
|
Portsmouth
|
D
|
ENG · Championship
|
| 10 Apr 1999 |
Bradford City
|
2–1
|
Portsmouth
|
H
|
ENG · Championship
|
| 05 Apr 1999 |
Portsmouth
|
0–1
|
Bristol City
|
A
|
ENG · Championship
|
| 03 Apr 1999 |
Wolverhampton Wanderers
|
2–0
|
Portsmouth
|
H
|
ENG · Championship
|
