| 4. Round | 09/09/1998 | Chelsea FC | - | Arsenal FC | 0:0 | ||||
| 5. Round | 12/09/1998 | Chelsea FC | - | Nottingham Forest | 2:1 | ||||
| 12. Round | 08/11/1998 | West Ham United | - | Chelsea FC | 1:1 | ||||
| 13. Round | 14/11/1998 | Chelsea FC | - | Wimbledon FC | 3:0 | ||||
| 17. Round | 12/12/1998 | Derby County | - | Chelsea FC | 2:2 | ||||
| 3. Round | 16/12/1998 | Manchester United | - | Chelsea FC | 1:1 |  |
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| 18. Round | 19/12/1998 | Chelsea FC | - | Tottenham Hotspur | 2:0 | ||||
| 22. Round | 16/01/1999 | Chelsea FC | - | Coventry City | 2:1 | ||||
| 25. Round | 17/02/1999 | Chelsea FC | - | Blackburn Rovers | 1:1 | |
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| 26. Round | 20/02/1999 | Nottingham Forest | - | Chelsea FC | 1:3 | ||||
| 27. Round | 27/02/1999 | Chelsea FC | - | Liverpool FC | 2:1 | ||||
| 30. Round | 21/03/1999 | Aston Villa | - | Chelsea FC | 0:3 | ||||
| 33. Round | 11/04/1999 | Wimbledon FC | - | Chelsea FC | 1:2 | ||||
| 35. Round | 25/04/1999 | Sheffield Wednesday | - | Chelsea FC | 0:0 | ||||
| 36. Round | 01/05/1999 | Chelsea FC | - | Everton FC | 3:1 | ||||
| 38. Round | 16/05/1999 | Chelsea FC | - | Derby County | 2:1 | |
France