| Date | Home | Score | Away | R | Tournament |
|---|---|---|---|---|---|
| 04 Dec 1999 |
Bradford City
|
1–1 |
|
D | ENG · Premier League |
| 30 Nov 1999 |
Middlesbrough
|
2–2 |
|
D | ENG · League Cup Round 4 |
| 27 Nov 1999 |
Middlesbrough
|
0–0 | Wimbledon | D | ENG · Premier League |
| 20 Nov 1999 |
Arsenal
|
5–1 |
|
H | ENG · Premier League |
| 06 Nov 1999 |
Middlesbrough
|
1–1 |
|
D | ENG · Premier League |
| 30 Oct 1999 |
Middlesbrough
|
2–1 |
|
H | ENG · Premier League |
| 24 Oct 1999 |
Watford
|
1–3 |
|
A | ENG · Premier League |
| 17 Oct 1999 |
Middlesbrough
|
2–0 |
|
H | ENG · Premier League |
| 13 Oct 1999 |
Middlesbrough
|
1–0 |
|
H | ENG · League Cup Round 3 |
| 03 Oct 1999 |
Newcastle United
|
2–1 |
|
H | ENG · Premier League |
| 25 Sep 1999 |
Middlesbrough
|
0–1 |
|
A | ENG · Premier League |
| 21 Sep 1999 |
Middlesbrough
|
2–1 |
|
H | ENG · League Cup Round 2 · Leg 2 |
| 19 Sep 1999 |
Leeds United
|
2–0 |
|
H | ENG · Premier League |
| 14 Sep 1999 |
Chesterfield
|
0–0 |
|
D | ENG · League Cup Round 2 · Leg 1 |
| 11 Sep 1999 |
Middlesbrough
|
3–2 |
|
H | ENG · Premier League |
| 28 Aug 1999 |
Aston Villa
|
1–0 |
|
H | ENG · Premier League |
| 24 Aug 1999 |
Middlesbrough
|
0–3 |
|
A | ENG · Premier League |
| 21 Aug 1999 |
Middlesbrough
|
1–0 |
|
H | ENG · Premier League |
| 14 Aug 1999 |
Derby County
|
1–3 |
|
A | ENG · Premier League |
| 10 Aug 1999 | Wimbledon | 2–3 |
|
A | ENG · Premier League |
| 07 Aug 1999 |
Middlesbrough
|
0–1 |
|
A | ENG · Premier League |
| 16 May 1999 |
West Ham United
|
4–0 |
|
H | ENG · Premier League |
| 09 May 1999 |
Middlesbrough
|
0–1 |
|
A | ENG · Premier League |
| 01 May 1999 |
Newcastle United
|
1–1 |
|
D | ENG · Premier League |
| 24 Apr 1999 |
Middlesbrough
|
1–6 |
|
A | ENG · Premier League |
| 17 Apr 1999 |
Coventry City
|
1–2 |
|
A | ENG · Premier League |
| 14 Apr 1999 |
Middlesbrough
|
0–0 |
|
D | ENG · Premier League |
| 10 Apr 1999 |
Middlesbrough
|
2–0 |
|
H | ENG · Premier League |
| 05 Apr 1999 |
Middlesbrough
|
3–1 | Wimbledon | H | ENG · Premier League |
| 03 Apr 1999 |
Blackburn Rovers
|
0–0 |
|
D | ENG · Premier League |
| 20 Mar 1999 |
Nottingham Forest
|
1–2 |
|
A | ENG · Premier League |
| 14 Mar 1999 |
Middlesbrough
|
3–0 |
|
H | ENG · Premier League |
| 27 Feb 1999 |
Sheffield Wednesday
|
3–1 |
|
H | ENG · Premier League |
| 20 Feb 1999 |
Middlesbrough
|
0–0 |
|
D | ENG · Premier League |
| 17 Feb 1999 |
Everton
|
5–0 |
|
H | ENG · Premier League |
| 06 Feb 1999 |
Liverpool
|
3–1 |
|
H | ENG · Premier League |
| 30 Jan 1999 |
Middlesbrough
|
0–0 |
|
D | ENG · Premier League |
| 16 Jan 1999 |
Leeds United
|
2–0 |
|
H | ENG · Premier League |
| 09 Jan 1999 |
Middlesbrough
|
0–0 |
|
D | ENG · Premier League |
| 03 Jan 1999 |
Manchester United
|
3–1 |
|
H | ENG · FA Cup Round 3 |