| 1. Round | 18/08/1956 | Burnley FC | - | Chelsea FC | 2:0 | ||||
| 6. Round | 05/09/1956 | Chelsea FC | - | Manchester United | 1:2 | ||||
| 27. Round | 19/01/1957 | Birmingham City | - | Chelsea FC | 0:1 | ||||
| 36. Round | 23/03/1957 | Chelsea FC | - | Sunderland AFC | 0:2 | ||||
| 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 | ||||
| 41. Round | 20/04/1957 | Chelsea FC | - | Everton FC | 5:1 | ||||
| 42. Round | 22/04/1957 | Chelsea FC | - | Newcastle United | 6:2 | ||||
| 23. Round | 27/04/1957 | Preston North End | - | Chelsea FC | 1:0 |
Ireland