| 6. Round | 12/09/1986 | Tottenham Hotspur | - | Chelsea FC | 1:3 |  |
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| 7. Round | 19/09/1986 | Chelsea FC | - | Nottingham Forest | 2:6 | ||||
| 11. Round | 18/10/1986 | Chelsea FC | - | Manchester City | 2:1 | |
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| 18. Round | 05/12/1986 | Chelsea FC | - | Wimbledon FC | 0:4 | ||||
| 26. Round | 23/01/1987 | Norwich City | - | Chelsea FC | 2:2 | ||||
| 27. Round | 06/02/1987 | Chelsea FC | - | Sheffield Wednesday | 2:0 | |
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| 25. Round | 09/02/1987 | Chelsea FC | - | Oxford United | 4:0 | |
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| 28. Round | 13/02/1987 | Coventry City | - | Chelsea FC | 3:0 | ||||
| 29. Round | 20/02/1987 | Chelsea FC | - | Manchester United | 1:1 | |
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| 30. Round | 27/02/1987 | Nottingham Forest | - | Chelsea FC | 0:1 | ||||
| 32. Round | 13/03/1987 | Manchester City | - | Chelsea FC | 1:2 | ||||
| 33. Round | 20/03/1987 | Chelsea FC | - | West Ham United | 1:0 | ||||
| 35. Round | 03/04/1987 | Chelsea FC | - | Everton FC | 1:2 | ||||
| 34. Round | 06/04/1987 | Charlton Athletic | - | Chelsea FC | 0:0 | ||||
| 36. Round | 10/04/1987 | Watford FC | - | Chelsea FC | 3:1 | ||||
| 37. Round | 17/04/1987 | Queens Park Rangers | - | Chelsea FC | 1:1 | ||||
| 38. Round | 19/04/1987 | Chelsea FC | - | Southampton FC | 1:1 | ||||
| 39. Round | 24/04/1987 | Newcastle United | - | Chelsea FC | 1:0 |
England