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Tottenham Hotspur 10th, 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 | 28 | 26 | 2 | 1.47 | 1.36 | | 1.47 | 28 | 12 |
| Away Record | 19 | 4 | 7 | 8 | 19 | 24 | -5 | 1.00 | 1.26 | | 1.00 | 19 | 12 |
| Overall Record | 38 | 11 | 14 | 13 | 47 | 50 | -3 | 1.23 | 1.31 | | 1.23 | 47 | 11 |
| English Premiership |
| No. | Date | Ven | Opponent | Result | HT | Attend |
| 1 | 07-Aug-99 | A | West Ham United | L | 0-1 | (0-1) | 26,010 |
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| 2 | 09-Aug-99 | H | Newcastle United | W | 3-1 | (2-1) | 28,701 |
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| 3 | 14-Aug-99 | H | Everton | W | 3-2 | (1-1) | 34,539 |
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| 4 | 21-Aug-99 | A | Sheffield Wednesday | W | 2-1 | (2-1) | 24,027 |
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| 5 | 28-Aug-99 | H | Leeds United | L | 1-2 | (1-0) | 36,012 |
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| 6 | 12-Sep-99 | A | Bradford City | D | 1-1 | (0-0) | 18,143 |
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| 7 | 19-Sep-99 | H | Coventry City | W | 3-2 | (1-0) | 35,224 |
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| 8 | 26-Sep-99 | A | Wimbledon | D | 1-1 | (0-0) | 17,368 |
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| 9 | 03-Oct-99 | H | Leicester City | L | 2-3 | (2-1) | 35,591 |
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| 10 | 16-Oct-99 | A | Derby County | W | 1-0 | (1-0) | 29,815 |
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| 11 | 23-Oct-99 | H | Manchester United | W | 3-1 | (2-1) | 36,072 |
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| 12 | 31-Oct-99 | A | Sunderland | L | 1-2 | (0-2) | 41,904 |
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| 13 | 07-Nov-99 | H | Arsenal | W | 2-1 | (2-1) | 36,085 |
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| 14 | 20-Nov-99 | A | Southampton | W | 1-0 | (0-0) | 15,248 |
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| 15 | 28-Nov-99 | A | Newcastle United | L | 1-2 | (1-1) | 36,460 |
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| 16 | 06-Dec-99 | H | West Ham United | D | 0-0 | (0-0) | 36,233 |
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| 17 | 18-Dec-99 | A | Middlesbrough | L | 1-2 | (1-1) | 33,129 |
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| 18 | 26-Dec-99 | H | Watford | W | 4-0 | (2-0) | 36,089 |
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| 19 | 29-Dec-99 | A | Aston Villa | D | 1-1 | (1-0) | 39,217 |
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| 20 | 03-Jan-00 | H | Liverpool | W | 1-0 | (1-0) | 36,044 |
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| 21 | 12-Jan-00 | A | Chelsea | L | 0-1 | (0-0) | 34,969 |
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| 22 | 15-Jan-00 | A | Everton | D | 2-2 | (2-1) | 34,144 |
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| 23 | 22-Jan-00 | H | Sheffield Wednesday | L | 0-1 | (0-1) | 35,897 |
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| 24 | 05-Feb-00 | H | Chelsea | L | 0-1 | (0-0) | 36,041 |
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| 25 | 12-Feb-00 | A | Leeds United | L | 0-1 | (0-1) | 40,127 |
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| 26 | 26-Feb-00 | A | Coventry City | W | 1-0 | (0-0) | 23,077 |
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| 27 | 04-Mar-00 | H | Bradford City | D | 1-1 | (1-1) | 35,472 |
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| 28 | 11-Mar-00 | H | Southampton | W | 7-2 | (4-2) | 36,024 |
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| 29 | 19-Mar-00 | A | Arsenal | L | 1-2 | (1-2) | 38,131 |
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| 30 | 25-Mar-00 | A | Watford | D | 1-1 | (0-0) | 20,050 |
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| 31 | 03-Apr-00 | H | Middlesbrough | L | 2-3 | (1-1) | 31,796 |
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| 32 | 09-Apr-00 | A | Liverpool | L | 0-2 | (0-1) | 44,536 |
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| 33 | 15-Apr-00 | H | Aston Villa | L | 2-4 | (1-0) | 35,304 |
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| 34 | 19-Apr-00 | A | Leicester City | W | 1-0 | (0-0) | 19,764 |
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| 35 | 22-Apr-00 | H | Wimbledon | W | 2-0 | (2-0) | 33,086 |
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| 36 | 29-Apr-00 | H | Derby County | D | 1-1 | (0-0) | 33,044 |
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| 37 | 06-May-00 | A | Manchester United | L | 1-3 | (1-3) | 61,229 |
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| 38 | 14-May-00 | H | Sunderland | W | 3-1 | (1-1) | 36,070 |
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| English FA Cup |
| Round | Date | Ven | Opponent | Result | HT | Attend |
| 3 | 12-Dec-99 | H | Newcastle United | D | 1-1 | (0-0) | 33,116 |
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| 3r | 22-Dec-99 | A | Newcastle United | L | 1-6 | (1-3) | 35,415 |
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| English League Cup |
| Round | Date | Ven | Opponent | Result | HT | Attend |
| 3 | 13-Oct-99 | H | Crewe Alexandra | W | 3-1 | (0-0) | 25,486 |
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| 4 | 01-Dec-99 | A | Fulham | L | 1-3 | (1-2) | 18,134 |
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| UEFA Cup |
| Round | Date | Ven | Opponent | Result | HT | Attend |
| 1 L1 | 16-Sep-99 | H | Zimbru Chisinau | W | 3-0 | (2-0) | 32,660 |
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| 1 L2 | 30-Sep-99 | A | Zimbru Chisinau | D | 0-0 | (0-0) | 4,500 |
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| 2 L1 | 28-Oct-99 | H | Kaiserslautern | W | 1-0 | (1-0) | 35,177 |
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| 2 L2 | 04-Nov-99 | A | Kaiserslautern | L | 0-2 | (0-0) | 28,000 |
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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 |
| W 3-1 | [2-2] | Manchester United | [1-2] | L 1-3 | 3 |
| W 2-1 | [1-3] | Arsenal | [0-0] | L 1-2 | 3 |
| L 1-2 | [3-3] | Leeds United | [0-2] | L 0-1 | 0 |
| W 1-0 | [2-1] | Liverpool | [2-3] | L 0-2 | 3 |
| L 0-1 | [2-2] | Chelsea | [0-2] | L 0-1 | 0 |
| L 2-4 | [1-0] | Aston Villa | [2-3] | D 1-1 | 1 |
| W 3-1 | - | Sunderland | - | L 1-2 | 3 |
| L 2-3 | [0-2] | Leicester City | [1-2] | W 1-0 | 3 |
| D 0-0 | [1-2] | West Ham United | [1-2] | L 0-1 | 1 |
| | Tottenham Hotspur | | |
| W 3-1 | [2-0] | Newcastle United | [1-1] | L 1-2 | 3 |
| L 2-3 | [0-3] | Middlesbrough | [0-0] | L 1-2 | 0 |
| W 3-2 | [4-1] | Everton | [1-0] | D 2-2 | 4 |
| W 3-2 | [0-0] | Coventry City | [1-1] | W 1-0 | 6 |
| W 7-2 | [3-0] | Southampton | [1-1] | W 1-0 | 6 |
| D 1-1 | [1-1] | Derby County | [1-0] | W 1-0 | 4 |
| D 1-1 | - | Bradford City | - | D 1-1 | 2 |
| W 2-0 | [0-0] | Wimbledon | [1-3] | D 1-1 | 4 |
| L 0-1 | [0-3] | Sheffield Wednesday | [0-0] | W 2-1 | 3 |
| W 4-0 | - | Watford | - | D 1-1 | 4 |
| Leading Scorers |
League Cup Europe |
| Iversen | | 17 | |  |  |  |  |  |  |  |  |  |  |  |  |  |  |  |  |  |
| Armstrong | | 14 | |  |  |  |  |  |  |  |  |  |  |  |  |  |  |
| Sherwood | | 10 | |  |  |  |  |  |  |  |  |  |  |
| Ginola | | 6 | |  |  |  |  |  |  |
| Leonhardsen | | 6 | |  |  |  |  |  |  |
| Anderton | | 3 | |  |  |  |
| Carr | | 3 | |  |  |  |
| Ferdinand | | 2 | |  |  |
| Perry | | 2 | |  |  |
| Clemence | | 1 | |  |
| Vega | | 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 | Europe |
 | 0 | 1 | 2 | 3 | 4 |
| 0 | 1 | 5 | 1 |
| 1 | 5 | 6 | 5 | 1 |
| 2 | 1 | 2 | 1 | 2 | 1 |
| 3 | | 3 | 2 |
| 4 | 1 |
| 5 |
| 6 |
| 7 | | | 1 |
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 | 0 | 1 | 2 | 3 | 4 | 5 | 6 |
| 0 |
| 1 | | 1 | | 1 | | | 1 |
| 2 |
| 3 | | 1 |
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 | 0 | 1 | 2 |
| 0 | 1 | | 1 |
| 1 | 1 |
| 2 |
| 3 | 1 |
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When the goals have been scored and conceded this season