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Middlesbrough 12th, English Premiership |
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| League Record 1998-1999 [for the same period] |
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| Pld | W | D | L | F | A | GD | GFA | GAA | | PpG | Pts | Rank |
| Home Record | 19 | 7 | 9 | 3 | 25 | 18 | 7 | 1.31 | 0.94 | | 1.57 | 30 | 10 |
| Away Record | 19 | 5 | 6 | 8 | 23 | 36 | -13 | 1.21 | 1.89 | | 1.10 | 21 | 8 |
| Overall Record | 38 | 12 | 15 | 11 | 48 | 54 | -6 | 1.26 | 1.42 | | 1.34 | 51 | 9 |
| English Premiership |
| No. | Date | Ven | Opponent | Result | HT | Attend |
| 1 | 07-Aug-99 | H | Bradford City | L | 0-1 | (0-0) | 33,762 |
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| 2 | 10-Aug-99 | A | Wimbledon | W | 3-2 | (2-1) | 11,036 |
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| 3 | 14-Aug-99 | A | Derby County | W | 3-1 | (2-1) | 24,045 |
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| 4 | 21-Aug-99 | H | Liverpool | W | 1-0 | (0-0) | 34,783 |
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| 5 | 24-Aug-99 | H | Leicester City | L | 0-3 | (0-2) | 33,126 |
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| 6 | 28-Aug-99 | A | Aston Villa | L | 0-1 | (0-1) | 28,728 |
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| 7 | 11-Sep-99 | H | Southampton | W | 3-2 | (1-1) | 32,165 |
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| 8 | 19-Sep-99 | A | Leeds United | L | 0-2 | (0-1) | 34,122 |
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| 9 | 25-Sep-99 | H | Chelsea | L | 0-1 | (0-0) | 34,183 |
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| 10 | 03-Oct-99 | A | Newcastle United | L | 1-2 | (0-2) | 36,412 |
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| 11 | 17-Oct-99 | H | West Ham United | W | 2-0 | (0-0) | 31,862 |
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| 12 | 24-Oct-99 | A | Watford | W | 3-1 | (2-0) | 16,081 |
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| 13 | 30-Oct-99 | H | Everton | W | 2-1 | (1-1) | 33,916 |
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| 14 | 06-Nov-99 | H | Sunderland | D | 1-1 | (0-0) | 34,793 |
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| 15 | 20-Nov-99 | A | Arsenal | L | 1-5 | (0-2) | 38,082 |
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| 16 | 27-Nov-99 | H | Wimbledon | D | 0-0 | (0-0) | 31,400 |
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| 17 | 04-Dec-99 | A | Bradford City | D | 1-1 | (1-0) | 17,708 |
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| 18 | 18-Dec-99 | H | Tottenham Hotspur | W | 2-1 | (1-1) | 33,129 |
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| 19 | 26-Dec-99 | A | Sheffield Wednesday | L | 0-1 | (0-1) | 28,531 |
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| 20 | 15-Jan-00 | H | Derby County | L | 1-4 | (0-1) | 32,745 |
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| 21 | 22-Jan-00 | A | Liverpool | D | 0-0 | (0-0) | 44,324 |
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| 22 | 29-Jan-00 | A | Manchester United | L | 0-1 | (0-0) | 61,267 |
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| 23 | 05-Feb-00 | A | Leicester City | L | 1-2 | (0-2) | 17,550 |
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| 24 | 14-Feb-00 | H | Aston Villa | L | 0-4 | (0-1) | 31,571 |
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| 25 | 19-Feb-00 | H | Coventry City | W | 2-0 | (2-0) | 32,798 |
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| 26 | 26-Feb-00 | H | Leeds United | D | 0-0 | (0-0) | 34,800 |
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| 27 | 04-Mar-00 | A | Southampton | D | 1-1 | (1-1) | 15,223 |
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| 28 | 12-Mar-00 | H | Arsenal | W | 2-1 | (0-0) | 34,244 |
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| 29 | 18-Mar-00 | A | Sunderland | D | 1-1 | (0-0) | 42,013 |
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| 30 | 25-Mar-00 | H | Sheffield Wednesday | W | 1-0 | (1-0) | 32,748 |
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| 31 | 03-Apr-00 | A | Tottenham Hotspur | W | 3-2 | (1-1) | 31,796 |
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| 32 | 10-Apr-00 | H | Manchester United | L | 3-4 | (1-0) | 34,775 |
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| 33 | 15-Apr-00 | A | Coventry City | L | 1-2 | (0-1) | 19,435 |
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| 34 | 22-Apr-00 | A | Chelsea | D | 1-1 | (1-1) | 34,467 |
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| 35 | 29-Apr-00 | A | West Ham United | W | 1-0 | (0-0) | 25,472 |
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| 36 | 02-May-00 | H | Newcastle United | D | 2-2 | (1-2) | 34,744 |
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| 37 | 06-May-00 | H | Watford | D | 1-1 | (1-0) | 32,930 |
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| 38 | 14-May-00 | A | Everton | W | 2-0 | (1-0) | 34,663 |
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| English FA Cup |
| Round | Date | Ven | Opponent | Result | HT | Attend |
| 3 | 11-Dec-99 | A | Wrexham | L | 1-2 | (1-0) | 11,755 |
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| English League Cup |
| Round | Date | Ven | Opponent | Result | HT | Attend |
| 2 L1 | 14-Sep-99 | A | Chesterfield | D | 0-0 | (0-0) | 4,941 |
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| 2 L2 | 21-Sep-99 | H | Chesterfield | W | 2-1 | (1-0) | 25,602 |
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| 3 | 13-Oct-99 | H | Watford | W | 1-0 | (0-0) | 8,847 |
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| 4 | 30-Nov-99 | H | Arsenal | D | 2-2 | (1-1) | 23,157 |
| [aet, pen 3-1] |
| QF | 14-Dec-99 | A | Tranmere Rovers | L | 1-2 | (0-1) | 10,581 |
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Home and away results against each team, listed in the current league table standings
| Home | 1998-1999 | Team | 1998-1999 | Away | Pts |
| L 3-4 | [0-1] | Manchester United | [3-2] | L 0-1 | 0 |
| W 2-1 | [1-6] | Arsenal | [1-1] | L 1-5 | 3 |
| D 0-0 | [0-0] | Leeds United | [0-2] | L 0-2 | 1 |
| W 1-0 | [1-3] | Liverpool | [1-3] | D 0-0 | 4 |
| L 0-1 | [0-0] | Chelsea | [0-2] | D 1-1 | 1 |
| L 0-4 | [0-0] | Aston Villa | [1-3] | L 0-1 | 0 |
| D 1-1 | - | Sunderland | - | D 1-1 | 2 |
| L 0-3 | [0-0] | Leicester City | [1-0] | L 1-2 | 0 |
| W 2-0 | [1-0] | West Ham United | [0-4] | W 1-0 | 6 |
| W 2-1 | [0-0] | Tottenham Hotspur | [3-0] | W 3-2 | 6 |
| D 2-2 | [2-2] | Newcastle United | [1-1] | L 1-2 | 1 |
| | Middlesbrough | | |
| W 2-1 | [2-2] | Everton | [0-5] | W 2-0 | 6 |
| W 2-0 | [2-0] | Coventry City | [2-1] | L 1-2 | 3 |
| W 3-2 | [3-0] | Southampton | [3-3] | D 1-1 | 4 |
| L 1-4 | [1-1] | Derby County | [1-2] | W 3-1 | 3 |
| L 0-1 | - | Bradford City | - | D 1-1 | 1 |
| D 0-0 | [3-1] | Wimbledon | [2-2] | W 3-2 | 4 |
| W 1-0 | [4-0] | Sheffield Wednesday | [1-3] | L 0-1 | 3 |
| D 1-1 | - | Watford | - | W 3-1 | 4 |
| Leading Scorers |
League Cup |
| Ricard | | 14 | |  |  |  |  |  |  |  |  |  |  |  |  |  |  |
| Deane | | 10 | |  |  |  |  |  |  |  |  |  |  |
| Ziege | | 7 | |  |  |  |  |  |  |  |
| Juninho | | 5 | |  |  |  |  |  |
| Campbell | | 4 | |  |  |  |  |
| Ince | | 4 | |  |  |  |  |
| Festa | | 2 | |  |  |
| Armstrong | | 1 | |  |
| Gascoigne | | 1 | |  |
| Pallister | | 1 | |  |
| Stockdale | | 1 | |  |
| Vickers | | 1 | |  |
| (own goals) | | 2 | |  |  |
Score distributions by match - goals scored by row, and goals conceded by column. Each box shows the number of this season's matches with the resulting scoreline.
| League | Cup |
 | 0 | 1 | 2 | 3 | 4 | 5 |
| 0 | 3 | 5 | 1 | 1 | 1 |
| 1 | 3 | 6 | 3 | | 1 | 1 |
| 2 | 3 | 3 | 1 |
| 3 | | 2 | 3 | | 1 |
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 | 0 | 1 | 2 |
| 0 | 1 |
| 1 | 1 | | 2 |
| 2 | | 1 | 1 |
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When the goals have been scored and conceded this season