| 1. Round | 18/08/1956 | Burnley FC | - | Chelsea FC | 2:0 | ||||
| 9. Round | 22/09/1956 | West Bromwich Albion | - | Chelsea FC | 2:1 |  |
|||
| 10. Round | 29/09/1956 | Chelsea FC | - | Portsmouth FC | 3:3 | ||||
| 11. Round | 06/10/1956 | Chelsea FC | - | Tottenham Hotspur | 2:4 | ||||
| 13. Round | 13/10/1956 | Everton FC | - | Chelsea FC | 0:3 | |
|||
| 13. Round | 20/10/1956 | Chelsea FC | - | Wolverhampton Wanderers | 3:3 | |
|||
| 25. Round | 26/12/1956 | Arsenal FC | - | Chelsea FC | 2:0 | ||||
| 27. Round | 19/01/1957 | Birmingham City | - | Chelsea FC | 0:1 | ||||
| 27. Round | 02/02/1957 | Chelsea FC | - | West Bromwich Albion | 2:4 | ||||
| 29. Round | 09/02/1957 | Portsmouth FC | - | Chelsea FC | 2:2 | ||||
| 30. Round | 20/02/1957 | Tottenham Hotspur | - | Chelsea FC | 3:4 | ||||
| 32. Round | 02/03/1957 | Wolverhampton Wanderers | - | Chelsea FC | 3:1 | |
|||
| 37. Round | 30/03/1957 | Luton Town | - | Chelsea FC | 0:4 | ||||
| 38. Round | 06/04/1957 | Chelsea FC | - | Aston Villa | 1:1 | ||||
| 39. Round | 13/04/1957 | Blackpool FC | - | Chelsea FC | 1:0 | ||||
| 40. Round | 19/04/1957 | Newcastle United | - | Chelsea FC | 1:2 | |
|||
| 42. Round | 22/04/1957 | Chelsea FC | - | Newcastle United | 6:2 | |
|||
| 23. Round | 27/04/1957 | Preston North End | - | Chelsea FC | 1:0 |
England