Middlesbrough
1999-2000
[squad stats] [appearance chart]
| Date | K.O. | Comp | Opponents | Ven | Res | Att | ||||
| Sat 7th Aug | --:-- | Prem | Bradford City | H | L | 0-1 | 33762 |  |
||
| Tue 10th Aug | --:-- | Prem | Wimbledon | A | W | 3-2 | 11036 | |
||
| Sat 14th Aug | --:-- | Prem | Derby County | A | W | 3-1 | 24045 | |
||
| Sat 21st Aug | --:-- | Prem | Liverpool | H | W | 1-0 | 34783 | |
||
| Tue 24th Aug | --:-- | Prem | Leicester City | H | L | 0-3 | 33126 | |
||
| Sat 28th Aug | --:-- | Prem | Aston Villa | A | L | 0-1 | 28728 | |
||
| Sat 11th Sep | --:-- | Prem | Southampton | H | W | 3-2 | 32165 | |
||
| Tue 14th Sep | --:-- | LC | Chesterfield | A | D | 0-0 | |
|||
| Sun 19th Sep | --:-- | Prem | Leeds United | A | L | 0-2 | 34122 | |
||
| Tue 21st Sep | --:-- | LC | Chesterfield | H | W | 2-1 | |
|||
| Sat 25th Sep | --:-- | Prem | Chelsea | H | L | 0-1 | 34183 | |
||
| Sun 3rd Oct | --:-- | Prem | Newcastle United | A | L | 1-2 | 36412 | |
||
| Wed 13th Oct | --:-- | LC | Watford | H | W | 1-0 | |
|||
| Sun 17th Oct | --:-- | Prem | West Ham United | H | W | 2-0 | 31862 | |
||
| Sun 24th Oct | --:-- | Prem | Watford | A | W | 3-1 | 16081 | |
||
| Sat 30th Oct | --:-- | Prem | Everton | H | W | 2-1 | 33916 | |
||
| Sat 6th Nov | --:-- | Prem | Sunderland | H | D | 1-1 | 34793 | |
||
| Sat 20th Nov | --:-- | Prem | Arsenal | A | L | 1-5 | 38082 | |
||
| Sat 27th Nov | --:-- | Prem | Wimbledon | H | D | 0-0 | 31400 | |
||
| Tue 30th Nov | --:-- | LC | Arsenal | H | D | 2-2 | |
|||
| Sat 4th Dec | --:-- | Prem | Bradford City | A | D | 1-1 | 17708 | |
||
| Sat 11th Dec | --:-- | FAC | Wrexham | A | L | 1-2 | |
|||
| Tue 14th Dec | --:-- | LC | Tranmere Rovers | A | L | 1-2 | |
|||
| Sat 18th Dec | --:-- | Prem | Tottenham Hotspur | H | W | 2-1 | 33129 | |
||
| Sun 26th Dec | --:-- | Prem | Sheffield Wednesday | A | L | 0-1 | 28531 | |
||
| Sat 15th Jan | --:-- | Prem | Derby County | H | L | 1-4 | 32745 | |
||
| Sat 22nd Jan | --:-- | Prem | Liverpool | A | D | 0-0 | 44324 | |
||
| Sat 29th Jan | --:-- | Prem | Manchester United | A | L | 0-1 | 61267 | |
||
| Sat 5th Feb | --:-- | Prem | Leicester City | A | L | 1-2 | 17550 | |
||
| Mon 14th Feb | --:-- | Prem | Aston Villa | H | L | 0-4 | 31571 | |
||
| Sat 19th Feb | --:-- | Prem | Coventry City | H | W | 2-0 | 32798 | |
||
| Sat 26th Feb | --:-- | Prem | Leeds United | H | D | 0-0 | 34800 | |
||
| Sat 4th Mar | --:-- | Prem | Southampton | A | D | 1-1 | 15223 | |
||
| Sun 12th Mar | --:-- | Prem | Arsenal | H | W | 2-1 | 34244 | |
||
| Sat 18th Mar | --:-- | Prem | Sunderland | A | D | 1-1 | 42013 | |
||
| Sat 25th Mar | --:-- | Prem | Sheffield Wednesday | H | W | 1-0 | 32748 | |
||
| Mon 3rd Apr | --:-- | Prem | Tottenham Hotspur | A | W | 3-2 | 31796 | |
||
| Mon 10th Apr | --:-- | Prem | Manchester United | H | L | 3-4 | 34775 | |
||
| Sat 15th Apr | --:-- | Prem | Coventry City | A | L | 1-2 | 19435 | |
||
| Sat 22nd Apr | --:-- | Prem | Chelsea | A | D | 1-1 | 34467 | |
||
| Sat 29th Apr | --:-- | Prem | West Ham United | A | W | 1-0 | 25472 | |
||
| Tue 2nd May | --:-- | Prem | Newcastle United | H | D | 2-2 | 34744 | |
||
| Sat 6th May | --:-- | Prem | Watford | H | D | 1-1 | 32930 | |
||
| Sun 14th May | --:-- | Prem | Everton | A | W | 2-0 | 34663 | |