| League | Date | Home Team | Score | Away Team | PL | 14-05-2000 | Tottenham | 3 - 1 | Sunderland | PL | 06-05-2000 | Man United | 3 - 1 | Tottenham | PL | 29-04-2000 | Tottenham | 1 - 1 | Derby | PL | 22-04-2000 | Tottenham | 2 - 0 | Wimbledon | PL | 19-04-2000 | Leicester | 0 - 1 | Tottenham | PL | 15-04-2000 | Tottenham | 2 - 4 | Aston Villa | PL | 09-04-2000 | Liverpool | 2 - 0 | Tottenham | PL | 03-04-2000 | Tottenham | 2 - 3 | Middlesbrough | PL | 25-03-2000 | Watford | 1 - 1 | Tottenham | PL | 19-03-2000 | Arsenal | 2 - 1 | Tottenham | PL | 11-03-2000 | Tottenham | 7 - 2 | Southampton | PL | 04-03-2000 | Tottenham | 1 - 1 | Bradford | PL | 26-02-2000 | Coventry | 0 - 1 | Tottenham | PL | 12-02-2000 | Leeds | 1 - 0 | Tottenham | PL | 05-02-2000 | Tottenham | 0 - 1 | Chelsea | PL | 22-01-2000 | Tottenham | 0 - 1 | Sheffield Weds | PL | 15-01-2000 | Everton | 2 - 2 | Tottenham | PL | 12-01-2000 | Chelsea | 1 - 0 | Tottenham | PL | 03-01-2000 | Tottenham | 1 - 0 | Liverpool | PL | 29-12-1999 | Aston Villa | 1 - 1 | Tottenham | PL | 26-12-1999 | Tottenham | 4 - 0 | Watford | PL | 18-12-1999 | Middlesbrough | 2 - 1 | Tottenham | PL | 06-12-1999 | Tottenham | 0 - 0 | West Ham | PL | 28-11-1999 | Newcastle | 2 - 1 | Tottenham | PL | 20-11-1999 | Southampton | 0 - 1 | Tottenham | PL | 07-11-1999 | Tottenham | 2 - 1 | Arsenal | PL | 31-10-1999 | Sunderland | 2 - 1 | Tottenham | PL | 23-10-1999 | Tottenham | 3 - 1 | Man United | PL | 16-10-1999 | Derby | 0 - 1 | Tottenham | PL | 03-10-1999 | Tottenham | 2 - 3 | Leicester | PL | 26-09-1999 | Wimbledon | 1 - 1 | Tottenham | PL | 19-09-1999 | Tottenham | 3 - 2 | Coventry | PL | 12-09-1999 | Bradford | 1 - 1 | Tottenham | PL | 28-08-1999 | Tottenham | 1 - 2 | Leeds | PL | 21-08-1999 | Sheffield Weds | 1 - 2 | Tottenham | PL | 14-08-1999 | Tottenham | 3 - 2 | Everton | PL | 09-08-1999 | Tottenham | 3 - 1 | Newcastle | PL | 07-08-1999 | West Ham | 1 - 0 | Tottenham |
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