| 1. Round | 03/08/2019 | Sunderland AFC | - | Oxford United | 1:1 | ||||
| 2. Round | 10/08/2019 | Ipswich Town | - | Sunderland AFC | 1:1 | ||||
| 3. Round | 17/08/2019 | Sunderland AFC | - | Portsmouth FC | 2:1 | ||||
| 6. Round | 31/08/2019 | Peterborough United | - | Sunderland AFC | 3:0 | ||||
| 8. Round | 14/09/2019 | Accrington Stanley | - | Sunderland AFC | 1:3 |  |
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| 9. Round | 17/09/2019 | Sunderland AFC | - | Rotherham United | 1:1 | |
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| 12. Round | 05/10/2019 | Lincoln City | - | Sunderland AFC | 2:0 | ||||
| 14. Round | 19/10/2019 | Wycombe Wanderers | - | Sunderland AFC | 1:0 | ||||
| 15. Round | 22/10/2019 | Sunderland AFC | - | Tranmere Rovers | 5:0 | ||||
| 16. Round | 26/10/2019 | Shrewsbury Town | - | Sunderland AFC | 1:0 | ||||
| 17. Round | 02/11/2019 | Sunderland AFC | - | Southend United | 1:0 | ||||
| 20. Round | 07/12/2019 | Gillingham FC | - | Sunderland AFC | 1:0 | ||||
| 23. Round | 26/12/2019 | Sunderland AFC | - | Bolton Wanderers | 0:0 | ||||
| 25. Round | 01/01/2020 | Fleetwood Town | - | Sunderland AFC | 1:1 | ||||
| 27. Round | 11/01/2020 | Sunderland AFC | - | Wycombe Wanderers | 4:0 |
Scotland