| 1. Round | 23/08/1958 | Portsmouth FC | - | West Ham United | 1:2 | ||||
| 2. Round | 25/08/1958 | West Ham United | - | Wolverhampton Wanderers | 2:0 | ||||
| 3. Round | 30/08/1958 | West Ham United | - | Aston Villa | 7:2 |  |
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| 4. Round | 03/09/1958 | Wolverhampton Wanderers | - | West Ham United | 1:1 | ||||
| 5. Round | 06/09/1958 | Luton Town | - | West Ham United | 4:1 | ||||
| 8. Round | 17/09/1958 | Manchester United | - | West Ham United | 4:1 |
England