| Date | Home | Score | Away | R | Tournament |
|---|---|---|---|---|---|
| 26 Dec 1999 |
Sheffield Wednesday
|
1–0 |
|
H | ENG · Premier League |
| 18 Dec 1999 |
Aston Villa
|
2–1 |
|
H | ENG · Premier League |
| 11 Dec 1999 |
Sheffield Wednesday
|
1–0 |
|
H | ENG · FA Cup Round 3 |
| 05 Dec 1999 |
Liverpool
|
4–1 |
|
H | ENG · Premier League |
| 30 Nov 1999 |
Bolton Wanderers
|
1–0 |
|
H | ENG · League Cup Round 4 |
| 21 Nov 1999 |
West Ham United
|
4–3 |
|
H | ENG · Premier League |
| 06 Nov 1999 |
Sheffield Wednesday
|
2–2 |
|
D | ENG · Premier League |
| 30 Oct 1999 |
Leicester City
|
3–0 |
|
H | ENG · Premier League |
| 23 Oct 1999 |
Sheffield Wednesday
|
0–0 |
|
D | ENG · Premier League |
| 16 Oct 1999 |
Leeds United
|
2–0 |
|
H | ENG · Premier League |
| 13 Oct 1999 |
Sheffield Wednesday
|
4–1 |
|
H | ENG · League Cup Round 3 |
| 02 Oct 1999 |
Sheffield Wednesday
|
5–1 | Wimbledon | H | ENG · Premier League |
| 25 Sep 1999 |
Sunderland
|
1–0 |
|
H | ENG · Premier League |
| 22 Sep 1999 |
Sheffield Wednesday
|
3–1 |
|
H | ENG · League Cup Round 2 · Leg 2 |
| 19 Sep 1999 |
Newcastle United
|
8–0 |
|
H | ENG · Premier League |
| 14 Sep 1999 |
Stoke City
|
0–0 |
|
D | ENG · League Cup Round 2 · Leg 1 |
| 11 Sep 1999 |
Sheffield Wednesday
|
0–2 |
|
A | ENG · Premier League |
| 28 Aug 1999 |
Southampton
|
2–0 |
|
H | ENG · Premier League |
| 25 Aug 1999 |
Sheffield Wednesday
|
0–2 |
|
A | ENG · Premier League |
| 21 Aug 1999 |
Sheffield Wednesday
|
1–2 |
|
A | ENG · Premier League |
| 14 Aug 1999 |
Bradford City
|
1–1 |
|
D | ENG · Premier League |
| 11 Aug 1999 |
Manchester United
|
4–0 |
|
H | ENG · Premier League |
| 07 Aug 1999 |
Sheffield Wednesday
|
1–2 |
|
A | ENG · Premier League |
| 16 May 1999 |
Charlton Athletic
|
0–1 |
|
A | ENG · Premier League |
| 08 May 1999 |
Sheffield Wednesday
|
1–0 |
|
H | ENG · Premier League |
| 01 May 1999 |
Nottingham Forest
|
2–0 |
|
H | ENG · Premier League |
| 25 Apr 1999 |
Sheffield Wednesday
|
0–0 |
|
D | ENG · Premier League |
| 21 Apr 1999 |
Sheffield Wednesday
|
1–1 |
|
D | ENG · Premier League |
| 17 Apr 1999 |
Manchester United
|
3–0 |
|
H | ENG · Premier League |
| 05 Apr 1999 |
Everton
|
1–2 |
|
A | ENG · Premier League |
| 03 Apr 1999 |
Sheffield Wednesday
|
1–2 |
|
A | ENG · Premier League |
| 20 Mar 1999 |
Southampton
|
1–0 |
|
H | ENG · Premier League |
| 13 Mar 1999 |
Sheffield Wednesday
|
0–2 |
|
A | ENG · Premier League |
| 09 Mar 1999 |
Arsenal
|
3–0 |
|
H | ENG · Premier League |
| 03 Mar 1999 |
Sheffield Wednesday
|
1–2 | Wimbledon | A | ENG · Premier League |
| 27 Feb 1999 |
Sheffield Wednesday
|
3–1 |
|
H | ENG · Premier League |
| 20 Feb 1999 |
Blackburn Rovers
|
1–4 |
|
A | ENG · Premier League |
| 13 Feb 1999 |
Sheffield Wednesday
|
0–1 |
|
A | ENG · FA Cup Round 5 |
| 06 Feb 1999 |
Leicester City
|
0–2 |
|
A | ENG · Premier League |
| 30 Jan 1999 |
Sheffield Wednesday
|
0–1 |
|
A | ENG · Premier League |