| 1. Round | 03/08/2019 | Reading FC | - | Sheffield Wednesday | 1:3 |  |
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| 3. Round | 17/08/2019 | Millwall FC | - | Sheffield Wednesday | 1:0 | ||||
| 4. Round | 20/08/2019 | Sheffield Wednesday | - | Luton Town | 1:0 | ||||
| 5. Round | 24/08/2019 | Preston North End | - | Sheffield Wednesday | 2:1 | ||||
| 6. Round | 31/08/2019 | Sheffield Wednesday | - | Queens Park Rangers | 1:2 | ||||
| 7. Round | 15/09/2019 | Huddersfield Town | - | Sheffield Wednesday | 0:2 | ||||
| 8. Round | 21/09/2019 | Sheffield Wednesday | - | Fulham FC | 1:1 | ||||
| 9. Round | 28/09/2019 | Middlesbrough FC | - | Sheffield Wednesday | 1:4 | ||||
| 10. Round | 01/10/2019 | Hull City | - | Sheffield Wednesday | 1:0 | ||||
| 11. Round | 05/10/2019 | Sheffield Wednesday | - | Wigan Athletic | 1:0 | ||||
| 14. Round | 26/10/2019 | Sheffield Wednesday | - | Leeds United | 0:0 | ||||
| 15. Round | 02/11/2019 | Blackburn Rovers | - | Sheffield Wednesday | 2:1 | ||||
| 16. Round | 09/11/2019 | Sheffield Wednesday | - | Swansea City | 2:2 | ||||
| 17. Round | 23/11/2019 | West Bromwich Albion | - | Sheffield Wednesday | 2:1 |
England