| 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 |  |
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| 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 | ||||
| 17. Round | 15/11/1958 | Preston North End | - | Portsmouth FC | 3:1 | ||||
| 18. Round | 22/11/1958 | Portsmouth FC | - | Burnley FC | 4:2 | ||||
| 19. Round | 29/11/1958 | Bolton Wanderers | - | Portsmouth FC | 2:1 | ||||
| 21. Round | 13/12/1958 | Everton FC | - | Portsmouth FC | 2:1 | ||||
| 22. Round | 20/12/1958 | West Ham United | - | Portsmouth FC | 6:0 | ||||
| 30. Round | 21/02/1959 | Tottenham Hotspur | - | Portsmouth FC | 4:4 | ||||
| 32. Round | 07/03/1959 | Portsmouth FC | - | Manchester City | 3:4 | ||||
| 29. Round | 11/03/1959 | Portsmouth FC | - | Newcastle United | 1:5 |
England