1998/99◄ Middlesbrough Results ►2000/01
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Ground: Riverside Stadium Division: Premier League |
Season 1999/00
League & Cup Results
| Game | Date | Opposition | Result | H/A | Venue | Competition |
| 1 | 07/08/1999 | Bradford City | Lost 0-1 | Home | Riverside Stadium | Premier League |
| 2 | 10/08/1999 | Wimbledon | Won 3-2 | Away | Selhurst Park | Premier League |
| 3 | 14/08/1999 | Derby County | Won 3-1 | Away | Pride Park | Premier League |
| 4 | 21/08/1999 | Liverpool | Won 1-0 | Home | Riverside Stadium | Premier League |
| 5 | 24/08/1999 | Leicester City | Lost 0-3 | Home | Riverside Stadium | Premier League |
| 6 | 28/08/1999 | Aston Villa | Lost 0-1 | Away | Villa Park | Premier League |
| 7 | 11/09/1999 | Southampton | Won 3-2 | Home | Riverside Stadium | Premier League |
| 8 | 14/09/1999 | Chesterfield | Drew 0-0 | Away | Saltergate | League Cup 2nd Round 1st Leg |
| 9 | 19/09/1999 | Leeds United | Lost 0-2 | Away | Elland Road | Premier League |
| 10 | 21/09/1999 | Chesterfield | Won 2-1 | Home | Riverside Stadium | League Cup 2nd Round 2nd Leg |
| Middlesbrough Won 2-1 on aggregate | ||||||
| 11 | 25/09/1999 | Chelsea | Lost 0-1 | Home | Riverside Stadium | Premier League |
| 12 | 03/10/1999 | Newcastle United | Lost 1-2 | Away | St James' Park | Premier League |
| 13 | 13/10/1999 | Watford | Won 1-0 | Home | Riverside Stadium | League Cup 3rd Round |
| 14 | 17/10/1999 | West Ham United | Won 2-0 | Home | Riverside Stadium | Premier League |
| 15 | 24/10/1999 | Watford | Won 3-1 | Away | Vicarage Road | Premier League |
| 16 | 30/10/1999 | Everton | Won 2-1 | Home | Riverside Stadium | Premier League |
| 17 | 06/11/1999 | Sunderland | Drew 1-1 | Home | Riverside Stadium | Premier League |
| 18 | 20/11/1999 | Arsenal | Lost 1-5 | Away | Highbury | Premier League |
| 19 | 27/11/1999 | Wimbledon | Drew 0-0 | Home | Riverside Stadium | Premier League |
| 20 | 30/11/1999 | Arsenal | Drew 2-2 | Home | Riverside Stadium | League Cup 4th Round |
| Middlesbrough Won 3-1 on Penalties | ||||||
| 21 | 04/12/1999 | Bradford City | Drew 1-1 | Away | Valley Parade | Premier League |
| 22 | 11/12/1999 | Wrexham | Lost 1-2 | Away | Racecourse Ground | FA Cup 3rd Round |
| 23 | 14/12/1999 | Tranmere Rovers | Lost 1-2 | Away | Prenton Park | League Cup Quarter Finals |
| 24 | 18/12/1999 | Tottenham Hotspur | Won 2-1 | Home | Riverside Stadium | Premier League |
| 25 | 26/12/1999 | Sheffield Wednesday | Lost 0-1 | Away | Hillsborough | Premier League |
| 26 | 15/01/2000 | Derby County | Lost 1-4 | Home | Riverside Stadium | Premier League |
| 27 | 22/01/2000 | Liverpool | Drew 0-0 | Away | Anfield | Premier League |
| 28 | 29/01/2000 | Manchester United | Lost 0-1 | Away | Old Trafford | Premier League |
| 29 | 05/02/2000 | Leicester City | Lost 1-2 | Away | Filbert Street | Premier League |
| 30 | 14/02/2000 | Aston Villa | Lost 0-4 | Home | Riverside Stadium | Premier League |
| 31 | 19/02/2000 | Coventry City | Won 2-0 | Home | Riverside Stadium | Premier League |
| 32 | 26/02/2000 | Leeds United | Drew 0-0 | Home | Riverside Stadium | Premier League |
| 33 | 04/03/2000 | Southampton | Drew 1-1 | Away | The Dell | Premier League |
| 34 | 12/03/2000 | Arsenal | Won 2-1 | Home | Riverside Stadium | Premier League |
| 35 | 18/03/2000 | Sunderland | Drew 1-1 | Away | Stadium of Light | Premier League |
| 36 | 25/03/2000 | Sheffield Wednesday | Won 1-0 | Home | Riverside Stadium | Premier League |
| 37 | 03/04/2000 | Tottenham Hotspur | Won 3-2 | Away | White Hart Lane | Premier League |
| 38 | 10/04/2000 | Manchester United | Lost 3-4 | Home | Riverside Stadium | Premier League |
| 39 | 15/04/2000 | Coventry City | Lost 1-2 | Away | Highfield Road | Premier League |
| 40 | 22/04/2000 | Chelsea | Drew 1-1 | Away | Stamford Bridge | Premier League |
| 41 | 29/04/2000 | West Ham United | Won 1-0 | Away | Boleyn Ground | Premier League |
| 42 | 02/05/2000 | Newcastle United | Drew 2-2 | Home | Riverside Stadium | Premier League |
| 43 | 06/05/2000 | Watford | Drew 1-1 | Home | Riverside Stadium | Premier League |
| 44 | 14/05/2000 | Everton | Won 2-0 | Away | Goodison Park | Premier League |
End of Season Review
| League Record | ||||||||
| Pos | Pld | W | D | L | F | A | GD | Pts |
| 12th | 38 | 14 | 10 | 14 | 46 | 52 | -6 | 52 |
| Click here for final League Standings | ||||||||
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Cup Record |
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| Competition | Round Reached | Knocked Out By |
| FA Cup | 3rd Round | Wrexham |
| Football League Cup | Quarter Finals | Tranmere Rovers |
Manager
Bryan Robson |
1998/99◄ Middlesbrough Results ►2000/01
