| 1. Round | 03/08/2019 | Sunderland AFC | - | Oxford United | 1:1 | ||||
| 2. Round | 10/08/2019 | Ipswich Town | - | Sunderland AFC | 1:1 | ||||
| 4. Round | 20/08/2019 | Rochdale AFC | - | Sunderland AFC | 1:2 | ||||
| 5. Round | 24/08/2019 | Sunderland AFC | - | AFC Wimbledon | 3:1 | ||||
| 8. Round | 14/09/2019 | Accrington Stanley | - | Sunderland AFC | 1:3 | ||||
| 9. Round | 17/09/2019 | Sunderland AFC | - | Rotherham United | 1:1 | ||||
| 11. Round | 28/09/2019 | Sunderland AFC | - | Milton Keynes Dons | 2:1 | ||||
| 12. Round | 05/10/2019 | Lincoln City | - | Sunderland AFC | 2:0 |
Scotland