4. Round | 02/09/1959 | Chelsea FC | - | Manchester United | 3:6 | ||||
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 | ||||
26. Round | 16/01/1960 | Burnley FC | - | Chelsea FC | 2:1 | ||||
27. Round | 23/01/1960 | Chelsea FC | - | Leeds United | 1:3 | ||||
34. Round | 19/03/1960 | Chelsea FC | - | Blackpool FC | 2:3 |