5. Round | 05/09/1959 | Chelsea FC | - | Burnley FC | 4:1 | ||||
6. Round | 09/09/1959 | Birmingham City | - | Chelsea FC | 1:1 | ||||
7. Round | 12/09/1959 | Leeds United | - | Chelsea FC | 2:1 | ||||
8. Round | 16/09/1959 | Chelsea FC | - | Birmingham City | 4:2 | ||||
9. Round | 19/09/1959 | Chelsea FC | - | West Ham United | 2:4 |