1. Round | 24/08/1957 | Tottenham Hotspur | - | Chelsea FC | 1:1 | ||||
2. Round | 28/08/1957 | Chelsea FC | - | Manchester City | 2:3 | ||||
3. Round | 31/08/1957 | Chelsea FC | - | Birmingham City | 5:1 | ||||
4. Round | 04/09/1957 | Manchester City | - | Chelsea FC | 5:2 | ||||
5. Round | 07/09/1957 | Everton FC | - | Chelsea FC | 3:0 | ||||
16. Round | 09/11/1957 | Chelsea FC | - | Luton Town | 1:3 | ||||
28. Round | 01/02/1958 | Burnley FC | - | Chelsea FC | 2:1 | ||||
29. Round | 08/02/1958 | Chelsea FC | - | Preston North End | 0:2 | ||||
42. Round | 26/04/1958 | Chelsea FC | - | Manchester United | 2:1 |