| Date | Home | Score | Away | R | Tournament |
|---|---|---|---|---|---|
| 01 Dec 1999 |
Aston Villa
|
4–0 |
|
H | ENG · League Cup Round 4 |
| 28 Nov 1999 |
Leeds United
|
1–0 |
|
H | ENG · Premier League |
| 20 Nov 1999 |
Southampton
|
0–1 |
|
A | ENG · Premier League |
| 06 Nov 1999 |
Aston Villa
|
0–1 |
|
A | ENG · Premier League |
| 30 Oct 1999 | Wimbledon | 1–1 |
|
D | ENG · Premier League |
| 23 Oct 1999 |
Southampton
|
1–1 |
|
D | ENG · Premier League |
| 16 Oct 1999 |
Leicester City
|
2–1 |
|
H | ENG · Premier League |
| 13 Oct 1999 |
Southampton
|
2–1 |
|
H | ENG · League Cup Round 3 |
| 04 Oct 1999 |
Southampton
|
3–3 |
|
D | ENG · Premier League |
| 25 Sep 1999 |
Manchester United
|
3–3 |
|
D | ENG · Premier League |
| 21 Sep 1999 |
Southampton
|
4–3 |
|
H | ENG · League Cup Round 2 · Leg 2 |
| 18 Sep 1999 |
Southampton
|
0–1 |
|
A | ENG · Premier League |
| 15 Sep 1999 |
Manchester City
|
0–0 |
|
D | ENG · League Cup Round 2 · Leg 1 |
| 11 Sep 1999 |
Middlesbrough
|
3–2 |
|
H | ENG · Premier League |
| 28 Aug 1999 |
Southampton
|
2–0 |
|
H | ENG · Premier League |
| 21 Aug 1999 |
Everton
|
4–1 |
|
H | ENG · Premier League |
| 15 Aug 1999 |
Southampton
|
4–2 |
|
H | ENG · Premier League |
| 11 Aug 1999 |
Southampton
|
0–3 |
|
A | ENG · Premier League |
| 07 Aug 1999 |
Coventry City
|
0–1 |
|
A | ENG · Premier League |
| 16 May 1999 |
Southampton
|
2–0 |
|
H | ENG · Premier League |
| 08 May 1999 | Wimbledon | 0–2 |
|
A | ENG · Premier League |
| 01 May 1999 |
Southampton
|
2–1 |
|
H | ENG · Premier League |
| 24 Apr 1999 |
Derby County
|
0–0 |
|
D | ENG · Premier League |
| 17 Apr 1999 |
Southampton
|
3–3 |
|
D | ENG · Premier League |
| 10 Apr 1999 |
Aston Villa
|
3–0 |
|
H | ENG · Premier League |
| 05 Apr 1999 |
Coventry City
|
1–0 |
|
H | ENG · Premier League |
| 03 Apr 1999 |
Southampton
|
0–0 |
|
D | ENG · Premier League |
| 20 Mar 1999 |
Southampton
|
1–0 |
|
H | ENG · Premier League |
| 14 Mar 1999 |
Middlesbrough
|
3–0 |
|
H | ENG · Premier League |
| 06 Mar 1999 |
Southampton
|
1–0 |
|
H | ENG · Premier League |
| 02 Mar 1999 |
Tottenham Hotspur
|
3–0 |
|
H | ENG · Premier League |
| 27 Feb 1999 |
Manchester United
|
2–1 |
|
H | ENG · Premier League |
| 20 Feb 1999 |
Southampton
|
2–1 |
|
H | ENG · Premier League |
| 06 Feb 1999 |
Chelsea
|
1–0 |
|
H | ENG · Premier League |
| 30 Jan 1999 |
Southampton
|
3–0 |
|
H | ENG · Premier League |
| 16 Jan 1999 |
Liverpool
|
7–1 |
|
H | ENG · Premier League |
| 13 Jan 1999 |
Fulham
|
1–0 |
|
H | ENG · FA Cup Round 3 |
| 09 Jan 1999 |
Southampton
|
3–1 |
|
H | ENG · Premier League |
| 02 Jan 1999 |
Southampton
|
1–1 |
|
D | ENG · FA Cup Round 3 |
| 28 Dec 1998 |
Nottingham Forest
|
1–1 |
|
D | ENG · Premier League |