| 1. Jornada | 07.08.1999 | Chelsea | - | Sunderland | 4:0 | ||||
| 13. Jornada | 30.10.1999 | Derby County | - | Chelsea | 3:1 | ||||
| 15. Jornada | 20.11.1999 | Everton | - | Chelsea | 1:1 | ||||
| 18. Jornada | 19.12.1999 | Chelsea | - | Leeds United | 0:2 |  |
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| 19. Jornada | 26.12.1999 | Southampton | - | Chelsea | 1:2 | ||||
| 20. Jornada | 29.12.1999 | Chelsea | - | Sheffield Wednesday | 3:0 | ||||
| 21. Jornada | 04.01.2000 | Coventry City | - | Chelsea | 2:2 | |
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| 2. Jornada | 08.01.2000 | Bradford City | - | Chelsea | 1:1 | ||||
| 5. Jornada | 12.01.2000 | Chelsea | - | Tottenham Hotspur | 1:0 | ||||
| 22. Jornada | 15.01.2000 | Chelsea | - | Leicester City | 1:1 | ||||
| 27. Jornada | 04.03.2000 | Newcastle United | - | Chelsea | 0:1 | ||||
| 28. Jornada | 11.03.2000 | Chelsea | - | Everton | 1:1 | ||||
| 29. Jornada | 18.03.2000 | West Ham United | - | Chelsea | 0:0 | ||||
| 31. Jornada | 01.04.2000 | Leeds United | - | Chelsea | 0:1 | ||||
| 32. Jornada | 12.04.2000 | Chelsea | - | Coventry City | 2:1 | ||||
| 36. Jornada | 29.04.2000 | Chelsea | - | Liverpool | 2:0 |  |
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| 37. Jornada | 06.05.2000 | Arsenal | - | Chelsea | 2:1 | ||||
| 38. Jornada | 14.05.2000 | Chelsea | - | Derby County | 4:0 | |
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Suiza
