| League | Date | Home Team | Score | Away Team |
|---|---|---|---|---|
| PL | 16-05-1999 | Man United | 2 - 1 | Tottenham |
| PL | 10-05-1999 | Tottenham | 2 - 2 | Chelsea |
| PL | 05-05-1999 | Tottenham | 1 - 3 | Arsenal |
| PL | 01-05-1999 | Liverpool | 3 - 2 | Tottenham |
| PL | 24-04-1999 | Tottenham | 1 - 2 | West Ham |
| PL | 20-04-1999 | Charlton | 1 - 4 | Tottenham |
| PL | 17-04-1999 | Notts Forest | 0 - 1 | Tottenham |
| PL | 05-04-1999 | Newcastle | 1 - 1 | Tottenham |
| PL | 03-04-1999 | Tottenham | 0 - 2 | Leicester |
| PL | 13-03-1999 | Tottenham | 1 - 0 | Aston Villa |
| PL | 10-03-1999 | Leeds | 2 - 0 | Tottenham |
| PL | 02-03-1999 | Tottenham | 3 - 0 | Southampton |
| PL | 27-02-1999 | Tottenham | 1 - 1 | Derby |
| PL | 20-02-1999 | Middlesbrough | 0 - 0 | Tottenham |
| PL | 06-02-1999 | Tottenham | 0 - 0 | Coventry |
| PL | 30-01-1999 | Blackburn | 1 - 1 | Tottenham |
| PL | 16-01-1999 | Tottenham | 0 - 0 | Wimbledon |
| PL | 09-01-1999 | Sheffield Weds | 0 - 0 | Tottenham |
| PL | 28-12-1998 | Tottenham | 4 - 1 | Everton |
| PL | 26-12-1998 | Coventry | 1 - 1 | Tottenham |
| PL | 19-12-1998 | Chelsea | 2 - 0 | Tottenham |
| PL | 12-12-1998 | Tottenham | 2 - 2 | Man United |
| PL | 05-12-1998 | Tottenham | 2 - 1 | Liverpool |
| PL | 28-11-1998 | West Ham | 2 - 1 | Tottenham |
| PL | 21-11-1998 | Tottenham | 2 - 0 | Notts Forest |
| PL | 14-11-1998 | Arsenal | 0 - 0 | Tottenham |
| PL | 07-11-1998 | Aston Villa | 3 - 2 | Tottenham |
| PL | 02-11-1998 | Tottenham | 2 - 2 | Charlton |
| PL | 24-10-1998 | Tottenham | 2 - 0 | Newcastle |
| PL | 19-10-1998 | Leicester | 2 - 1 | Tottenham |
| PL | 03-10-1998 | Derby | 0 - 1 | Tottenham |
| PL | 26-09-1998 | Tottenham | 3 - 3 | Leeds |
| PL | 19-09-1998 | Southampton | 1 - 1 | Tottenham |
| PL | 13-09-1998 | Tottenham | 0 - 3 | Middlesbrough |
| PL | 09-09-1998 | Tottenham | 2 - 1 | Blackburn |
| PL | 29-08-1998 | Everton | 0 - 1 | Tottenham |
| PL | 22-08-1998 | Tottenham | 0 - 3 | Sheffield Weds |
| PL | 15-08-1998 | Wimbledon | 3 - 1 | Tottenham |