| 1. Round | 24/08/1957 | Portsmouth FC | - | Burnley FC | 0:0 | ||||
| 6. Round | 11/09/1957 | Newcastle United | - | Portsmouth FC | 2:0 | ||||
| 7. Round | 14/09/1957 | Manchester City | - | Portsmouth FC | 2:1 | ||||
| 23. Round | 25/12/1957 | Chelsea FC | - | Portsmouth FC | 7:4 |  |
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| 24. Round | 26/12/1957 | Portsmouth FC | - | Chelsea FC | 3:0 | |
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| 25. Round | 28/12/1957 | Portsmouth FC | - | Preston North End | 0:2 | ||||
| 26. Round | 11/01/1958 | Sheffield Wednesday | - | Portsmouth FC | 4:2 | ||||
| 28. Round | 01/02/1958 | Nottingham Forest | - | Portsmouth FC | 2:0 | ||||
| 29. Round | 08/02/1958 | Portsmouth FC | - | Bolton Wanderers | 2:2 | ||||
| 36. Round | 29/03/1958 | Portsmouth FC | - | Arsenal FC | 5:4 | |
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| 37. Round | 04/04/1958 | Portsmouth FC | - | Birmingham City | 3:2 | |
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| 38. Round | 05/04/1958 | Wolverhampton Wanderers | - | Portsmouth FC | 1:0 | ||||
| 39. Round | 07/04/1958 | Birmingham City | - | Portsmouth FC | 4:1 | ||||
| 40. Round | 12/04/1958 | Portsmouth FC | - | Blackpool FC | 1:2 | ||||
| 32. Round | 16/04/1958 | Portsmouth FC | - | Manchester United | 3:3 | ||||
| 41. Round | 19/04/1958 | Luton Town | - | Portsmouth FC | 2:1 | ||||
| 42. Round | 26/04/1958 | Portsmouth FC | - | Sunderland AFC | 0:2 |
England