| 1. Round | 07/08/1999 | Chelsea FC | - | Sunderland AFC | 4:0 |  |
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| 3. Round | 14/08/1999 | Leicester City | - | Chelsea FC | 2:2 | ||||
| 7. Round | 11/09/1999 | Chelsea FC | - | Newcastle United | 1:0 | ||||
| 8. Round | 18/09/1999 | Watford FC | - | Chelsea FC | 1:0 | |
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| 9. Round | 25/09/1999 | Middlesbrough FC | - | Chelsea FC | 0:1 | ||||
| 10. Round | 03/10/1999 | Chelsea FC | - | Manchester United | 5:0 | ||||
| 11. Round | 16/10/1999 | Liverpool FC | - | Chelsea FC | 1:0 | ||||
| 12. Round | 23/10/1999 | Chelsea FC | - | Arsenal FC | 2:3 | |
England