| 16. Round | 07/11/1959 | Chelsea FC | - | Blackburn Rovers | 3:1 | ||||
| 17. Round | 14/11/1959 | Manchester City | - | Chelsea FC | 1:1 | ||||
| 18. Round | 21/11/1959 | Chelsea FC | - | Arsenal FC | 1:3 | ||||
| 19. Round | 28/11/1959 | Wolverhampton Wanderers | - | Chelsea FC | 3:1 | ||||
| 20. Round | 05/12/1959 | Chelsea FC | - | Sheffield Wednesday | 0:4 |
England