| 19. Round | 29/11/1958 | West Bromwich Albion | - | Tottenham Hotspur | 4:3 |  |
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| 20. Round | 06/12/1958 | Nottingham Forest | - | West Bromwich Albion | 1:1 | ||||
| 21. Round | 13/12/1958 | West Bromwich Albion | - | Chelsea FC | 4:0 | |
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| 23. Round | 26/12/1958 | West Bromwich Albion | - | Leeds United | 1:2 | ||||
| 24. Round | 27/12/1958 | Leeds United | - | West Bromwich Albion | 0:1 | ||||
| 25. Round | 03/01/1959 | Bolton Wanderers | - | West Bromwich Albion | 2:1 |
England