| 11. Round | 04/10/1958 | Portsmouth FC | - | Tottenham Hotspur | 1:1 | ||||
| 24. Round | 27/12/1958 | Wolverhampton Wanderers | - | Portsmouth FC | 7:0 | ||||
| 25. Round | 03/01/1959 | Portsmouth FC | - | Nottingham Forest | 0:1 | ||||
| 26. Round | 17/01/1959 | Chelsea FC | - | Portsmouth FC | 2:2 | ||||
| 27. Round | 31/01/1959 | Portsmouth FC | - | Blackpool FC | 1:2 | ||||
| 28. Round | 07/02/1959 | Blackburn Rovers | - | Portsmouth FC | 2:1 | ||||
| 30. Round | 21/02/1959 | Tottenham Hotspur | - | Portsmouth FC | 4:4 | ||||
| 31. Round | 28/02/1959 | Leeds United | - | Portsmouth FC | 1:1 | ||||
| 32. Round | 07/03/1959 | Portsmouth FC | - | Manchester City | 3:4 |
England