| 1. Round | 24/08/1957 | Tottenham Hotspur | - | Chelsea FC | 1:1 | ||||
| 2. Round | 28/08/1957 | Chelsea FC | - | Manchester City | 2:3 | ||||
| 6. Round | 11/09/1957 | Chelsea FC | - | West Bromwich Albion | 2:2 | ||||
| 7. Round | 14/09/1957 | Newcastle United | - | Chelsea FC | 1:3 | ||||
| 8. Round | 18/09/1957 | West Bromwich Albion | - | Chelsea FC | 1:1 | ||||
| 9. Round | 21/09/1957 | Chelsea FC | - | Burnley FC | 6:1 | ||||
| 10. Round | 28/09/1957 | Preston North End | - | Chelsea FC | 5:2 | ||||
| 11. Round | 05/10/1957 | Chelsea FC | - | Sheffield Wednesday | 1:0 | ||||
| 12. Round | 12/10/1957 | Chelsea FC | - | Aston Villa | 4:2 | ||||
| 13. Round | 19/10/1957 | Wolverhampton Wanderers | - | Chelsea FC | 2:1 | ||||
| 14. Round | 26/10/1957 | Chelsea FC | - | Arsenal FC | 0:0 | ||||
| 15. Round | 02/11/1957 | Blackpool FC | - | Chelsea FC | 2:1 |
Ireland