| 1. Jornada | 07.08.1999 | West Ham United | - | Tottenham Hotspur | 1:0 | ||||
| 2. Jornada | 09.08.1999 | Tottenham Hotspur | - | Newcastle United | 3:1 | ||||
| 6. Jornada | 28.08.1999 | Tottenham Hotspur | - | Leeds United | 1:2 | ||||
| 8. Jornada | 19.09.1999 | Tottenham Hotspur | - | Coventry City | 3:2 | ||||
| 9. Jornada | 26.09.1999 | Wimbledon FC | - | Tottenham Hotspur | 1:1 | ||||
| 13. Jornada | 31.10.1999 | Sunderland | - | Tottenham Hotspur | 2:1 | ||||
| 14. Jornada | 07.11.1999 | Tottenham Hotspur | - | Arsenal | 2:1 | ||||
| 15. Jornada | 20.11.1999 | Southampton | - | Tottenham Hotspur | 0:1 | ||||
| 16. Jornada | 28.11.1999 | Newcastle United | - | Tottenham Hotspur | 2:1 | ||||
| 17. Jornada | 06.12.1999 | Tottenham Hotspur | - | West Ham United | 0:0 | ||||
| 19. Jornada | 26.12.1999 | Tottenham Hotspur | - | Watford FC | 4:0 | ||||
| 25. Jornada | 12.02.2000 | Leeds United | - | Tottenham Hotspur | 1:0 |
Portugal