| 8. Round | 18/09/1957 | Leicester City | - | Sheffield Wednesday | 4:1 | ||||
| 13. Round | 19/10/1957 | Luton Town | - | Sheffield Wednesday | 2:0 | ||||
| 14. Round | 26/10/1957 | Sheffield Wednesday | - | Sunderland AFC | 3:3 | ||||
| 15. Round | 02/11/1957 | Bolton Wanderers | - | Sheffield Wednesday | 5:4 | ||||
| 16. Round | 09/11/1957 | Sheffield Wednesday | - | Leeds United | 3:2 | ||||
| 17. Round | 16/11/1957 | Manchester United | - | Sheffield Wednesday | 2:1 | ||||
| 18. Round | 23/11/1957 | Sheffield Wednesday | - | Arsenal FC | 2:0 | ||||
| 21. Round | 14/12/1957 | Wolverhampton Wanderers | - | Sheffield Wednesday | 4:3 | ||||
| 22. Round | 21/12/1957 | Sheffield Wednesday | - | Manchester City | 4:5 | ||||
| 26. Round | 11/01/1958 | Sheffield Wednesday | - | Portsmouth FC | 4:2 | ||||
| 27. Round | 18/01/1958 | West Bromwich Albion | - | Sheffield Wednesday | 3:1 | ||||
| 28. Round | 01/02/1958 | Sheffield Wednesday | - | Tottenham Hotspur | 2:0 | ||||
| 30. Round | 15/02/1958 | Sheffield Wednesday | - | Chelsea FC | 2:3 | ||||
| 31. Round | 22/02/1958 | Blackpool FC | - | Sheffield Wednesday | 2:2 | ||||
| 32. Round | 01/03/1958 | Sheffield Wednesday | - | Luton Town | 2:1 | ||||
| 33. Round | 08/03/1958 | Sunderland AFC | - | Sheffield Wednesday | 3:3 |
Scotland