1. Round | 23/08/1958 | Portsmouth FC | - | West Ham United | 1:2 | ||||
2. Round | 25/08/1958 | Aston Villa | - | Portsmouth FC | 3:2 | ||||
3. Round | 30/08/1958 | Nottingham Forest | - | Portsmouth FC | 5:0 | ||||
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 |