| 1. Round | 23/08/1958 | Portsmouth FC | - | West Ham United | 1:2 | ||||
| 4. Round | 03/09/1958 | Portsmouth FC | - | Aston Villa | 5:2 | ||||
| 5. Round | 06/09/1958 | Portsmouth FC | - | Chelsea FC | 2:2 | ||||
| 6. Round | 10/09/1958 | West Bromwich Albion | - | Portsmouth FC | 1:2 | ||||
| 7. Round | 13/09/1958 | Blackpool FC | - | Portsmouth FC | 1:1 | ||||
| 8. Round | 17/09/1958 | Portsmouth FC | - | West Bromwich Albion | 2:6 | ||||
| 9. Round | 20/09/1958 | Portsmouth FC | - | Blackburn Rovers | 2:1 | ||||
| 10. Round | 27/09/1958 | Newcastle United | - | Portsmouth FC | 2:0 | ||||
| 11. Round | 04/10/1958 | Portsmouth FC | - | Tottenham Hotspur | 1:1 | ||||
| 12. Round | 11/10/1958 | Portsmouth FC | - | Leeds United | 2:0 | ||||
| 13. Round | 18/10/1958 | Manchester City | - | Portsmouth FC | 3:2 | ||||
| 14. Round | 25/10/1958 | Portsmouth FC | - | Luton Town | 2:2 | ||||
| 15. Round | 01/11/1958 | Birmingham City | - | Portsmouth FC | 2:2 | ||||
| 16. Round | 08/11/1958 | Portsmouth FC | - | Leicester City | 4:1 | ||||
| 23. Round | 26/12/1958 | Portsmouth FC | - | Wolverhampton Wanderers | 3:5 | ||||
| 40. Round | 18/04/1959 | Portsmouth FC | - | Bolton Wanderers | 0:1 | ||||
| 33. Round | 22/04/1959 | Luton Town | - | Portsmouth FC | 3:1 |
England