| 1. Round | 18/08/1956 | Burnley FC | - | Chelsea FC | 2:0 | ||||
| 2. Round | 22/08/1956 | Sheffield Wednesday | - | Chelsea FC | 4:0 | ||||
| 3. Round | 25/08/1956 | Chelsea FC | - | Preston North End | 1:0 | ||||
| 5. Round | 01/09/1956 | Leeds United | - | Chelsea FC | 0:0 | ||||
| 7. Round | 08/09/1956 | Cardiff City | - | Chelsea FC | 1:1 | ||||
| 8. Round | 15/09/1956 | Chelsea FC | - | Birmingham City | 1:0 | ||||
| 9. Round | 19/09/1956 | Chelsea FC | - | Sheffield Wednesday | 0:0 | ||||
| 10. Round | 29/09/1956 | Chelsea FC | - | Portsmouth FC | 3:3 | ||||
| 11. Round | 06/10/1956 | Chelsea FC | - | Tottenham Hotspur | 2:4 | ||||
| 15. Round | 27/10/1956 | Bolton Wanderers | - | Chelsea FC | 2:2 |
England