| 1. Round | 22/08/1959 | West Bromwich Albion | - | Manchester United | 3:2 | ||||
| 3. Round | 29/08/1959 | Preston North End | - | West Bromwich Albion | 1:1 | ||||
| 4. Round | 02/09/1959 | West Bromwich Albion | - | Tottenham Hotspur | 1:2 | ||||
| 5. Round | 05/09/1959 | West Bromwich Albion | - | Leicester City | 5:0 |  |
|||
| 6. Round | 09/09/1959 | West Bromwich Albion | - | Newcastle United | 2:2 | ||||
| 10. Round | 26/09/1959 | West Ham United | - | West Bromwich Albion | 4:1 | ||||
| 13. Round | 17/10/1959 | Bolton Wanderers | - | West Bromwich Albion | 0:0 |
England