| 4. Round | 07/09/1990 | Chelsea FC | - | Sunderland AFC | 3:2 | ||||
| 5. Round | 14/09/1990 | Arsenal FC | - | Chelsea FC | 4:1 | ||||
| 8. Round | 06/10/1990 | Southampton FC | - | Chelsea FC | 3:3 | ||||
| 10. Round | 27/10/1990 | Liverpool FC | - | Chelsea FC | 2:0 | ||||
| 11. Round | 02/11/1990 | Chelsea FC | - | Aston Villa | 1:0 | ||||
| 12. Round | 09/11/1990 | Chelsea FC | - | Norwich City | 1:1 | ||||
| 15. Round | 30/11/1990 | Chelsea FC | - | Tottenham Hotspur | 3:2 |  |
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| 16. Round | 07/12/1990 | Chelsea FC | - | Crystal Palace | 2:1 | ||||
| 20. Round | 28/12/1990 | Luton Town | - | Chelsea FC | 2:0 | ||||
| 21. Round | 31/12/1990 | Chelsea FC | - | Everton FC | 1:2 | ||||
| 23. Round | 18/01/1991 | Sunderland AFC | - | Chelsea FC | 1:0 | ||||
| 24. Round | 01/02/1991 | Chelsea FC | - | Arsenal FC | 2:1 | ||||
| 26. Round | 15/02/1991 | Chelsea FC | - | Wimbledon FC | 0:0 |
England