| 9. Round | 25/09/1999 | Middlesbrough FC | - | Chelsea FC | 0:1 |  |
|||
| 11. Round | 16/10/1999 | Liverpool FC | - | Chelsea FC | 1:0 | ||||
| 13. Round | 30/10/1999 | Derby County | - | Chelsea FC | 3:1 |  |
|||
| 17. Round | 04/12/1999 | Sunderland AFC | - | Chelsea FC | 4:1 | ||||
| 20. Round | 29/12/1999 | Chelsea FC | - | Sheffield Wednesday | 3:0 | ||||
| 5. Round | 12/01/2000 | Chelsea FC | - | Tottenham Hotspur | 1:0 | ||||
| 23. Round | 22/01/2000 | Aston Villa | - | Chelsea FC | 0:0 | ||||
| 24. Round | 05/02/2000 | Tottenham Hotspur | - | Chelsea FC | 0:1 | |
|||
| 25. Round | 12/02/2000 | Chelsea FC | - | Wimbledon FC | 3:1 | ||||
| 26. Round | 26/02/2000 | Chelsea FC | - | Watford FC | 2:1 | ||||
| 31. Round | 01/04/2000 | Leeds United | - | Chelsea FC | 0:1 | ||||
| 33. Round | 15/04/2000 | Sheffield Wednesday | - | Chelsea FC | 1:0 | ||||
| 34. Round | 22/04/2000 | Chelsea FC | - | Middlesbrough FC | 1:1 | ||||
| 35. Round | 24/04/2000 | Manchester United | - | Chelsea FC | 3:2 | |
|||
| 37. Round | 06/05/2000 | Arsenal FC | - | Chelsea FC | 2:1 |
France