| 11. Round | 20/09/1969 | Leeds United | - | Chelsea FC | 2:0 | ||||
| 12. Round | 27/09/1969 | Chelsea FC | - | Arsenal FC | 3:0 | ||||
| 13. Round | 04/10/1969 | Sunderland AFC | - | Chelsea FC | 0:0 | ||||
| 15. Round | 11/10/1969 | Chelsea FC | - | Derby County | 2:2 | ||||
| 17. Round | 25/10/1969 | Newcastle United | - | Chelsea FC | 0:1 | ||||
| 18. Round | 01/11/1969 | Chelsea FC | - | Coventry City | 1:0 | ||||
| 30. Round | 15/04/1970 | Burnley FC | - | Chelsea FC | 3:1 |
Scotland