| 3. Round | 29/08/1959 | Sheffield Wednesday | - | Manchester City | 1:0 | ||||
| 4. Round | 02/09/1959 | Sheffield Wednesday | - | Wolverhampton Wanderers | 2:2 | ||||
| 5. Round | 05/09/1959 | Blackburn Rovers | - | Sheffield Wednesday | 3:1 | ||||
| 7. Round | 12/09/1959 | Sheffield Wednesday | - | Blackpool FC | 5:0 | ||||
| 8. Round | 16/09/1959 | Sheffield Wednesday | - | Nottingham Forest | 0:1 | ||||
| 9. Round | 19/09/1959 | Everton FC | - | Sheffield Wednesday | 2:1 |  |
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| 10. Round | 26/09/1959 | Sheffield Wednesday | - | Luton Town | 2:0 | ||||
| 20. Round | 05/12/1959 | Chelsea FC | - | Sheffield Wednesday | 0:4 | ||||
| 40. Round | 18/04/1960 | Sheffield Wednesday | - | Newcastle United | 2:0 | ||||
| 41. Round | 23/04/1960 | Sheffield Wednesday | - | Birmingham City | 2:4 |
England