1. Jornada | 07.08.1999 | Chelsea | - | Sunderland | 4:0 | ||||
3. Jornada | 14.08.1999 | Leicester City | - | Chelsea | 2:2 | ||||
7. Jornada | 11.09.1999 | Chelsea | - | Newcastle United | 1:0 | ||||
8. Jornada | 18.09.1999 | Watford FC | - | Chelsea | 1:0 | ||||
9. Jornada | 25.09.1999 | Middlesbrough | - | Chelsea | 0:1 | ||||
10. Jornada | 03.10.1999 | Chelsea | - | Manchester United | 5:0 | ||||
11. Jornada | 16.10.1999 | Liverpool | - | Chelsea | 1:0 | ||||
12. Jornada | 23.10.1999 | Chelsea | - | Arsenal | 2:3 |