| Date | Home | Score | Away | R | Tournament |
|---|---|---|---|---|---|
| 19 Feb 2000 |
Middlesbrough
|
2–0 |
|
H | ENG · Premier League |
| 12 Feb 2000 |
Coventry City
|
3–2 |
|
H | ENG · Premier League |
| 05 Feb 2000 |
Manchester United
|
3–2 |
|
H | ENG · Premier League |
| 29 Jan 2000 |
Coventry City
|
2–3 |
|
A | ENG · FA Cup Round 5 |
| 22 Jan 2000 |
Derby County
|
0–0 |
|
D | ENG · Premier League |
| 15 Jan 2000 |
Coventry City
|
2–0 | Wimbledon | H | ENG · Premier League |
| 08 Jan 2000 |
Coventry City
|
3–0 |
|
H | ENG · FA Cup Round 4 |
| 04 Jan 2000 |
Coventry City
|
2–2 |
|
D | ENG · Premier League |
| 26 Dec 1999 |
Coventry City
|
3–2 |
|
H | ENG · Premier League |
| 18 Dec 1999 |
Liverpool
|
2–0 |
|
H | ENG · Premier League |
| 11 Dec 1999 |
Norwich City
|
1–3 |
|
A | ENG · FA Cup Round 3 |
| 04 Dec 1999 |
Southampton
|
0–0 |
|
D | ENG · Premier League |
| 27 Nov 1999 |
Coventry City
|
0–1 |
|
A | ENG · Premier League |
| 22 Nov 1999 |
Coventry City
|
2–1 |
|
H | ENG · Premier League |
| 06 Nov 1999 |
Bradford City
|
1–1 |
|
D | ENG · Premier League |
| 31 Oct 1999 |
Coventry City
|
4–0 |
|
H | ENG · Premier League |
| 23 Oct 1999 |
Sheffield Wednesday
|
0–0 |
|
D | ENG · Premier League |
| 16 Oct 1999 |
Coventry City
|
4–1 |
|
H | ENG · Premier League |
| 02 Oct 1999 |
Everton
|
1–1 |
|
D | ENG · Premier League |
| 25 Sep 1999 |
Coventry City
|
1–0 |
|
H | ENG · Premier League |
| 22 Sep 1999 |
Coventry City
|
3–1 |
|
H | ENG · League Cup Round 2 · Leg 2 |
| 19 Sep 1999 |
Tottenham Hotspur
|
3–2 |
|
H | ENG · Premier League |
| 14 Sep 1999 |
Tranmere Rovers
|
5–1 |
|
H | ENG · League Cup Round 2 · Leg 1 |
| 11 Sep 1999 |
Coventry City
|
3–4 |
|
A | ENG · Premier League |
| 29 Aug 1999 |
Sunderland
|
1–1 |
|
D | ENG · Premier League |
| 25 Aug 1999 |
Coventry City
|
1–2 |
|
A | ENG · Premier League |
| 21 Aug 1999 |
Coventry City
|
2–0 |
|
H | ENG · Premier League |
| 14 Aug 1999 | Wimbledon | 1–1 |
|
D | ENG · Premier League |
| 11 Aug 1999 |
Leicester City
|
1–0 |
|
H | ENG · Premier League |
| 07 Aug 1999 |
Coventry City
|
0–1 |
|
A | ENG · Premier League |
| 16 May 1999 |
Coventry City
|
2–2 |
|
D | ENG · Premier League |
| 08 May 1999 |
Derby County
|
0–0 |
|
D | ENG · Premier League |
| 01 May 1999 |
Coventry City
|
2–1 | Wimbledon | H | ENG · Premier League |
| 24 Apr 1999 |
Leicester City
|
1–0 |
|
H | ENG · Premier League |
| 17 Apr 1999 |
Coventry City
|
1–2 |
|
A | ENG · Premier League |
| 11 Apr 1999 |
Everton
|
2–0 |
|
H | ENG · Premier League |
| 05 Apr 1999 |
Coventry City
|
1–0 |
|
H | ENG · Premier League |
| 03 Apr 1999 |
Sheffield Wednesday
|
1–2 |
|
A | ENG · Premier League |
| 20 Mar 1999 |
Arsenal
|
2–0 |
|
H | ENG · Premier League |
| 13 Mar 1999 |
Coventry City
|
1–1 |
|
D | ENG · Premier League |