| 1. Round | 22/08/1959 | Arsenal FC | - | Sheffield Wednesday | 0:1 | ||||
| 2. Round | 26/08/1959 | Wolverhampton Wanderers | - | Sheffield Wednesday | 3:1 | ||||
| 3. Round | 29/08/1959 | Sheffield Wednesday | - | Manchester City | 1:0 | ||||
| 4. Round | 02/09/1959 | Sheffield Wednesday | - | Wolverhampton Wanderers | 2:2 |  |
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| 5. Round | 05/09/1959 | Blackburn Rovers | - | Sheffield Wednesday | 3:1 | ||||
| 6. Round | 09/09/1959 | Nottingham Forest | - | Sheffield Wednesday | 2:1 | |
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| 7. Round | 12/09/1959 | Sheffield Wednesday | - | Blackpool FC | 5:0 | |
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| 8. Round | 16/09/1959 | Sheffield Wednesday | - | Nottingham Forest | 0:1 | ||||
| 10. Round | 26/09/1959 | Sheffield Wednesday | - | Luton Town | 2:0 |
England