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Wimbledon 18th, 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 | 7 | 5 | 22 | 21 | 1 | 1.15 | 1.10 | | 1.47 | 28 | 13 |
| Away Record | 19 | 3 | 5 | 11 | 18 | 42 | -24 | 0.94 | 2.21 | | 0.73 | 14 | 17 |
| Overall Record | 38 | 10 | 12 | 16 | 40 | 63 | -23 | 1.05 | 1.65 | | 1.10 | 42 | 16 |
| English Premiership |
| No. | Date | Ven | Opponent | Result | HT | Attend |
| 1 | 07-Aug-99 | A | Watford | W | 3-2 | (2-1) | 15,511 |
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| 2 | 10-Aug-99 | H | Middlesbrough | L | 2-3 | (1-2) | 11,036 |
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| 3 | 14-Aug-99 | H | Coventry City | D | 1-1 | (0-0) | 10,635 |
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| 4 | 21-Aug-99 | A | Newcastle United | D | 3-3 | (1-2) | 35,809 |
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| 5 | 25-Aug-99 | A | Everton | L | 0-4 | (0-1) | 32,818 |
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| 6 | 28-Aug-99 | H | Chelsea | L | 0-1 | (0-0) | 22,167 |
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| 7 | 11-Sep-99 | H | Derby County | D | 2-2 | (0-1) | 12,820 |
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| 8 | 18-Sep-99 | A | Manchester United | D | 1-1 | (1-0) | 55,189 |
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| 9 | 26-Sep-99 | H | Tottenham Hotspur | D | 1-1 | (0-0) | 17,368 |
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| 10 | 02-Oct-99 | A | Sheffield Wednesday | L | 1-5 | (1-2) | 18,077 |
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| 11 | 16-Oct-99 | H | Bradford City | W | 3-2 | (2-1) | 10,029 |
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| 12 | 23-Oct-99 | A | Aston Villa | D | 1-1 | (1-1) | 27,160 |
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| 13 | 30-Oct-99 | H | Southampton | D | 1-1 | (0-0) | 15,754 |
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| 14 | 07-Nov-99 | H | Leeds United | W | 2-0 | (1-0) | 18,747 |
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| 15 | 20-Nov-99 | A | Leicester City | L | 1-2 | (1-1) | 18,255 |
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| 16 | 27-Nov-99 | A | Middlesbrough | D | 0-0 | (0-0) | 31,400 |
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| 17 | 04-Dec-99 | H | Watford | W | 5-0 | (2-0) | 14,021 |
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| 18 | 18-Dec-99 | A | Arsenal | D | 1-1 | (1-0) | 38,052 |
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| 19 | 26-Dec-99 | H | West Ham United | D | 2-2 | (1-1) | 20,394 |
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| 20 | 28-Dec-99 | A | Liverpool | L | 1-3 | (0-0) | 44,107 |
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| 21 | 03-Jan-00 | H | Sunderland | W | 1-0 | (1-0) | 17,621 |
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| 22 | 15-Jan-00 | A | Coventry City | L | 0-2 | (0-0) | 19,012 |
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| 23 | 22-Jan-00 | H | Newcastle United | W | 2-0 | (0-0) | 22,118 |
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| 24 | 06-Feb-00 | H | Everton | L | 0-3 | (0-0) | 13,172 |
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| 25 | 12-Feb-00 | A | Chelsea | L | 1-3 | (0-0) | 34,826 |
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| 26 | 26-Feb-00 | H | Manchester United | D | 2-2 | (1-1) | 26,129 |
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| 27 | 04-Mar-00 | A | Derby County | L | 0-4 | (0-0) | 28,384 |
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| 28 | 11-Mar-00 | H | Leicester City | W | 2-1 | (1-0) | 14,316 |
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| 29 | 19-Mar-00 | A | Leeds United | L | 1-4 | (1-3) | 39,256 |
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| 30 | 26-Mar-00 | A | West Ham United | L | 1-2 | (0-1) | 22,438 |
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| 31 | 01-Apr-00 | H | Arsenal | L | 1-3 | (1-2) | 25,858 |
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| 32 | 08-Apr-00 | A | Sunderland | L | 1-2 | (0-0) | 41,592 |
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| 33 | 12-Apr-00 | H | Sheffield Wednesday | L | 0-2 | (0-1) | 8,248 |
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| 34 | 16-Apr-00 | H | Liverpool | L | 1-2 | (0-1) | 26,102 |
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| 35 | 22-Apr-00 | A | Tottenham Hotspur | L | 0-2 | (0-2) | 33,086 |
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| 36 | 30-Apr-00 | A | Bradford City | L | 0-3 | (0-1) | 18,276 |
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| 37 | 06-May-00 | H | Aston Villa | D | 2-2 | (1-0) | 19,188 |
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| 38 | 14-May-00 | A | Southampton | L | 0-2 | (0-0) | 15,249 |
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| English FA Cup |
| Round | Date | Ven | Opponent | Result | HT | Attend |
| 3 | 11-Dec-99 | H | Barnsley | W | 1-0 | (1-0) | 4,505 |
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| 4 | 08-Jan-00 | A | Fulham | L | 0-3 | (0-2) | 16,877 |
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| English League Cup |
| Round | Date | Ven | Opponent | Result | HT | Attend |
| 2 L1 | 14-Sep-99 | A | Cardiff City | D | 1-1 | (0-1) | 7,613 |
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| 2 L2 | 21-Sep-99 | H | Cardiff City | W | 3-1 | (0-1) | 2,772 |
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| 3 | 12-Oct-99 | H | Sunderland | W | 3-2 | (0-0) | 5,061 |
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| 4 | 30-Nov-99 | A | Huddersfield Town | W | 2-1 | (0-1) | 13,312 |
| [aet] |
| QF | 14-Dec-99 | A | Bolton Wanderers | L | 1-2 | (1-2) | 9,463 |
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| Pld | W | D | L | F | A | GD | GFA | GAA | | PpG | Pts | Rank |
| August | 6 | 1 | 2 | 3 | 9 | 14 | -5 | 1.50 | 2.33 | | 0.83 | 5 | 17 |
| September | 3 | 0 | 3 | 0 | 4 | 4 | 0 | 1.33 | 1.33 | | 1.00 | 3 | 11 |
| October | 4 | 1 | 2 | 1 | 6 | 9 | -3 | 1.50 | 2.25 | | 1.25 | 5 | 11 |
| November | 3 | 1 | 1 | 1 | 3 | 2 | 1 | 1.00 | 0.66 | | 1.33 | 4 | 10 |
| December | 4 | 1 | 2 | 1 | 9 | 6 | 3 | 2.25 | 1.50 | | 1.25 | 5 | 10 |
| January | 3 | 2 | 0 | 1 | 3 | 2 | 1 | 1.00 | 0.66 | | 2.00 | 6 | 4 |
| February | 3 | 0 | 1 | 2 | 3 | 8 | -5 | 1.00 | 2.66 | | 0.33 | 1 | 19 |
| March | 4 | 1 | 0 | 3 | 4 | 11 | -7 | 1.00 | 2.75 | | 0.75 | 3 | 18 |
| April | 6 | 0 | 0 | 6 | 3 | 14 | -11 | 0.50 | 2.33 | | 0.00 | 0 | 20 |
| May | 2 | 0 | 1 | 1 | 2 | 4 | -2 | 1.00 | 2.00 | | 0.50 | 1 | 16 |
Home and away results against each team, listed in the current league table standings
| Home | 1998-1999 | Team | 1998-1999 | Away | Pts |
| D 2-2 | [1-1] | Manchester United | [1-5] | D 1-1 | 2 |
| L 1-3 | [1-0] | Arsenal | [1-5] | D 1-1 | 1 |
| W 2-0 | [1-1] | Leeds United | [2-2] | L 1-4 | 3 |
| L 1-2 | [1-0] | Liverpool | [0-3] | L 1-3 | 0 |
| L 0-1 | [1-2] | Chelsea | [0-3] | L 1-3 | 0 |
| D 2-2 | [0-0] | Aston Villa | [0-2] | D 1-1 | 2 |
| W 1-0 | - | Sunderland | - | L 1-2 | 3 |
| W 2-1 | [0-1] | Leicester City | [1-1] | L 1-2 | 3 |
| D 2-2 | [0-0] | West Ham United | [4-3] | L 1-2 | 1 |
| D 1-1 | [3-1] | Tottenham Hotspur | [0-0] | L 0-2 | 1 |
| W 2-0 | [1-1] | Newcastle United | [1-3] | D 3-3 | 4 |
| L 2-3 | [2-2] | Middlesbrough | [1-3] | D 0-0 | 1 |
| L 0-3 | [1-2] | Everton | [1-1] | L 0-4 | 0 |
| D 1-1 | [2-1] | Coventry City | [1-2] | L 0-2 | 1 |
| D 1-1 | [0-2] | Southampton | [1-3] | L 0-2 | 1 |
| D 2-2 | [2-1] | Derby County | [0-0] | L 0-4 | 1 |
| W 3-2 | - | Bradford City | - | L 0-3 | 3 |
| | Wimbledon | | |
| L 0-2 | [2-1] | Sheffield Wednesday | [2-1] | L 1-5 | 0 |
| W 5-0 | - | Watford | - | W 3-2 | 6 |
| Leading Scorers |
League Cup |
| Cort | | 15 | |  |  |  |  |  |  |  |  |  |  |  |  |  |  |  |
| Hartson | | 9 | |  |  |  |  |  |  |  |  |  |
| Gayle | | 7 | |  |  |  |  |  |  |  |
| Earle | | 5 | |  |  |  |  |  |
| Euell | | 5 | |  |  |  |  |  |
| Hughes | | 4 | |  |  |  |  |
| Ainsworth | | 2 | |  |  |
| Ardley | | 2 | |  |  |
| Lund | | 2 | |  |  |
| Andresen | | 1 | |  |
| Badir | | 1 | |  |
| Hreidarsson | | 1 | |  |
| Kimble | | 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 | 1 | 1 | 4 | 2 | 2 |
| 1 | 1 | 6 | 4 | 3 | 1 | 1 |
| 2 | 2 | 1 | 4 | 1 |
| 3 | | | 2 | 1 |
| 4 |
| 5 | 1 |
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 | 0 | 1 | 2 | 3 |
| 0 | | | | 1 |
| 1 | 1 | 1 | 1 |
| 2 | | 1 |
| 3 | | 1 | 1 |
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When the goals have been scored and conceded this season
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