| 9. Round | 20/09/1985 | Chelsea FC | - | Arsenal FC | 2:1 | ||||
| 10. Round | 27/09/1985 | Watford FC | - | Chelsea FC | 3:1 | ||||
| 11. Round | 05/10/1985 | Manchester City | - | Chelsea FC | 0:1 | ||||
| 12. Round | 12/10/1985 | Chelsea FC | - | Everton FC | 2:1 | ||||
| 13. Round | 19/10/1985 | Oxford United | - | Chelsea FC | 2:1 | ||||
| 16. Round | 08/11/1985 | Chelsea FC | - | Nottingham Forest | 4:2 |  |
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| 17. Round | 15/11/1985 | Newcastle United | - | Chelsea FC | 1:3 | ||||
| 18. Round | 22/11/1985 | Chelsea FC | - | Aston Villa | 2:1 | ||||
| 34. Round | 10/01/1986 | Chelsea FC | - | Luton Town | 1:0 | ||||
| 28. Round | 31/01/1986 | Chelsea FC | - | Leicester City | 2:2 | ||||
| 29. Round | 07/02/1986 | Chelsea FC | - | Oxford United | 1:4 | ||||
| 35. Round | 28/03/1986 | Chelsea FC | - | West Ham United | 0:4 | ||||
| 36. Round | 30/03/1986 | Queens Park Rangers | - | Chelsea FC | 6:0 | ||||
| 38. Round | 08/04/1986 | Manchester United | - | Chelsea FC | 1:2 | ||||
| 39. Round | 11/04/1986 | Nottingham Forest | - | Chelsea FC | 0:0 | ||||
| 25. Round | 14/04/1986 | West Ham United | - | Chelsea FC | 1:2 | ||||
| 40. Round | 18/04/1986 | Chelsea FC | - | Newcastle United | 1:1 | ||||
| 41. Round | 25/04/1986 | Aston Villa | - | Chelsea FC | 3:1 |
England