Middlesbrough FC in the Premier League
Competitions| Match Day | Opponent | For | Against | ||
|---|---|---|---|---|---|
| 18-12-99 | Tottenham Hotspur | Home | 2 | 1 | Info |
| 04-12-99 | Bradford City | Away | 1 | 1 | Info |
| 27-11-99 | Wimbledon | Home | 0 | 0 | Info |
| 20-11-99 | Arsenal | Away | 1 | 5 | Info |
| 06-11-99 | Sunderland | Home | 1 | 1 | Info |
| 30-10-99 | Everton | Home | 2 | 1 | Info |
| 24-10-99 | Watford | Away | 3 | 1 | Info |
| 17-10-99 | West Ham United | Home | 2 | 0 | Info |
| 03-10-99 | Newcastle United | Away | 1 | 2 | Info |
| 25-09-99 | Chelsea | Home | 0 | 1 | Info |
| 19-09-99 | Leeds United | Away | 0 | 2 | Info |
| 11-09-99 | Southampton | Home | 3 | 2 | Info |
| 28-08-99 | Aston Villa | Away | 0 | 1 | Info |
| 24-08-99 | Leicester City | Home | 0 | 3 | Info |
| 21-08-99 | Liverpool | Home | 1 | 0 | Info |
| 14-08-99 | Derby County | Away | 3 | 1 | Info |
| 10-08-99 | Wimbledon | Away | 3 | 2 | Info |
| 07-08-99 | Bradford City | Home | 0 | 1 | Info |
| 16-05-99 | West Ham United | Away | 0 | 4 | Info |
| 09-05-99 | Manchester United | Home | 0 | 1 | Info |
| 01-05-99 | Newcastle United | Away | 1 | 1 | Info |
| 24-04-99 | Arsenal | Home | 1 | 6 | Info |
| 17-04-99 | Coventry City | Away | 2 | 1 | Info |
| 14-04-99 | Chelsea | Home | 0 | 0 | Info |
| 10-04-99 | Charlton Athletic | Home | 2 | 0 | Info |
| 05-04-99 | Wimbledon | Home | 3 | 1 | Info |
| 03-04-99 | Blackburn Rovers | Away | 0 | 0 | Info |
| 20-03-99 | Nottingham Forest | Away | 2 | 1 | Info |
| 14-03-99 | Southampton | Home | 3 | 0 | Info |
| 27-02-99 | Sheffield Wednesday | Away | 1 | 3 | Info |
| 20-02-99 | Tottenham Hotspur | Home | 0 | 0 | Info |
| 17-02-99 | Everton | Away | 0 | 5 | Info |
| 06-02-99 | Liverpool | Away | 1 | 3 | Info |
| 30-01-99 | Leicester City | Home | 0 | 0 | Info |
| 16-01-99 | Leeds United | Away | 0 | 2 | Info |
| 09-01-99 | Aston Villa | Home | 0 | 0 | Info |
| 28-12-98 | Derby County | Away | 1 | 2 | Info |
| 26-12-98 | Liverpool | Home | 1 | 3 | Info |
| 19-12-98 | Manchester United | Away | 3 | 2 | Info |
| 12-12-98 | West Ham United | Home | 1 | 0 | Info |
| 06-12-98 | Newcastle United | Home | 2 | 2 | Info |
| 29-11-98 | Arsenal | Away | 1 | 1 | Info |
| 21-11-98 | Coventry City | Home | 2 | 0 | Info |
| 14-11-98 | Charlton Athletic | Away | 1 | 1 | Info |
| 07-11-98 | Southampton | Away | 3 | 3 | Info |
| 01-11-98 | Nottingham Forest | Home | 1 | 1 | Info |
| 24-10-98 | Wimbledon | Away | 2 | 2 | Info |
| 17-10-98 | Blackburn Rovers | Home | 2 | 1 | Info |
| 03-10-98 | Sheffield Wednesday | Home | 4 | 0 | Info |
| 26-09-98 | Chelsea | Away | 0 | 2 | Info |