2. Round | 10/08/2019 | Middlesbrough FC | - | Brentford FC | 0:1 | ||||
3. Round | 17/08/2019 | Blackburn Rovers | - | Middlesbrough FC | 1:0 | ||||
6. Round | 31/08/2019 | Bristol City | - | Middlesbrough FC | 2:2 | ||||
7. Round | 14/09/2019 | Middlesbrough FC | - | Reading FC | 1:0 | ||||
8. Round | 21/09/2019 | Cardiff City | - | Middlesbrough FC | 1:0 | ||||
9. Round | 28/09/2019 | Middlesbrough FC | - | Sheffield Wednesday | 1:4 | ||||
10. Round | 01/10/2019 | Middlesbrough FC | - | Preston North End | 1:1 | ||||
11. Round | 04/10/2019 | Birmingham City | - | Middlesbrough FC | 2:1 | ||||
15. Round | 02/11/2019 | Derby County | - | Middlesbrough FC | 2:0 | ||||
16. Round | 09/11/2019 | Queens Park Rangers | - | Middlesbrough FC | 2:2 | ||||
17. Round | 24/11/2019 | Middlesbrough FC | - | Hull City | 2:2 | ||||
18. Round | 27/11/2019 | Middlesbrough FC | - | Barnsley FC | 1:0 | ||||
42. Round | 08/07/2020 | Millwall FC | - | Middlesbrough FC | 0:2 | ||||
44. Round | 14/07/2020 | Reading FC | - | Middlesbrough FC | 1:2 | ||||
45. Round | 18/07/2020 | Middlesbrough FC | - | Cardiff City | 1:3 | ||||
46. Round | 22/07/2020 | Sheffield Wednesday | - | Middlesbrough FC | 1:2 |