| 9. Round | 04/10/1986 | Chelsea FC | - | Charlton Athletic | 0:1 | ||||
| 10. Round | 11/10/1986 | West Ham United | - | Chelsea FC | 5:3 | ||||
| 11. Round | 18/10/1986 | Chelsea FC | - | Manchester City | 2:1 | ||||
| 12. Round | 25/10/1986 | Arsenal FC | - | Chelsea FC | 3:1 | ||||
| 13. Round | 31/10/1986 | Chelsea FC | - | Watford FC | 0:0 | ||||
| 14. Round | 07/11/1986 | Everton FC | - | Chelsea FC | 2:2 | ||||
| 15. Round | 14/11/1986 | Aston Villa | - | Chelsea FC | 0:0 | ||||
| 19. Round | 13/12/1986 | Liverpool FC | - | Chelsea FC | 3:0 |
Scotland