| Date | Home | Score | Away | R | Tournament |
|---|---|---|---|---|---|
| 18 Nov 2000 |
Middlesbrough
|
0–3 |
|
A | ENG · Premier League |
| 11 Nov 2000 |
Manchester United
|
2–1 |
|
H | ENG · Premier League |
| 04 Nov 2000 |
Middlesbrough
|
0–1 |
|
A | ENG · Premier League |
| 31 Oct 2000 | Wimbledon | 1–0 |
|
H | ENG · League Cup Round 3 |
| 28 Oct 2000 |
Ipswich Town
|
2–1 |
|
H | ENG · Premier League |
| 21 Oct 2000 |
Charlton Athletic
|
1–0 |
|
H | ENG · Premier League |
| 16 Oct 2000 |
Middlesbrough
|
1–3 |
|
A | ENG · Premier League |
| 30 Sep 2000 |
Southampton
|
1–3 |
|
A | ENG · Premier League |
| 26 Sep 2000 |
Macclesfield Town
|
1–3 |
|
A | ENG · League Cup Round 2 · Leg 2 |
| 23 Sep 2000 |
Middlesbrough
|
1–1 |
|
D | ENG · Premier League |
| 19 Sep 2000 |
Middlesbrough
|
2–1 |
|
H | ENG · League Cup Round 2 · Leg 1 |
| 17 Sep 2000 |
Manchester City
|
1–1 |
|
D | ENG · Premier League |
| 09 Sep 2000 |
Middlesbrough
|
1–2 |
|
A | ENG · Premier League |
| 06 Sep 2000 |
Derby County
|
3–3 |
|
D | ENG · Premier League |
| 26 Aug 2000 |
Middlesbrough
|
1–2 |
|
A | ENG · Premier League |
| 22 Aug 2000 |
Middlesbrough
|
1–1 |
|
D | ENG · Premier League |
| 19 Aug 2000 |
Coventry City
|
1–3 |
|
A | ENG · Premier League |
| 14 May 2000 |
Everton
|
0–2 |
|
A | ENG · Premier League |
| 06 May 2000 |
Middlesbrough
|
1–1 |
|
D | ENG · Premier League |
| 02 May 2000 |
Middlesbrough
|
2–2 |
|
D | ENG · Premier League |
| 29 Apr 2000 |
West Ham United
|
0–1 |
|
A | ENG · Premier League |
| 22 Apr 2000 |
Chelsea
|
1–1 |
|
D | ENG · Premier League |
| 15 Apr 2000 |
Coventry City
|
2–1 |
|
H | ENG · Premier League |
| 10 Apr 2000 |
Middlesbrough
|
3–4 |
|
A | ENG · Premier League |
| 03 Apr 2000 |
Tottenham Hotspur
|
2–3 |
|
A | ENG · Premier League |
| 25 Mar 2000 |
Middlesbrough
|
1–0 |
|
H | ENG · Premier League |
| 18 Mar 2000 |
Sunderland
|
1–1 |
|
D | ENG · Premier League |
| 12 Mar 2000 |
Middlesbrough
|
2–1 |
|
H | ENG · Premier League |
| 04 Mar 2000 |
Southampton
|
1–1 |
|
D | ENG · Premier League |
| 26 Feb 2000 |
Middlesbrough
|
0–0 |
|
D | ENG · Premier League |
| 19 Feb 2000 |
Middlesbrough
|
2–0 |
|
H | ENG · Premier League |
| 14 Feb 2000 |
Middlesbrough
|
0–4 |
|
A | ENG · Premier League |
| 05 Feb 2000 |
Leicester City
|
2–1 |
|
H | ENG · Premier League |
| 29 Jan 2000 |
Manchester United
|
1–0 |
|
H | ENG · Premier League |
| 22 Jan 2000 |
Liverpool
|
0–0 |
|
D | ENG · Premier League |
| 15 Jan 2000 |
Middlesbrough
|
1–4 |
|
A | ENG · Premier League |
| 26 Dec 1999 |
Sheffield Wednesday
|
1–0 |
|
H | ENG · Premier League |
| 18 Dec 1999 |
Middlesbrough
|
2–1 |
|
H | ENG · Premier League |
| 14 Dec 1999 |
Tranmere Rovers
|
2–1 |
|
H | ENG · League Cup Round 5 |
| 11 Dec 1999 |
Wrexham
|
2–1 |
|
H | ENG · FA Cup Round 3 |