| 4. Round | 30/08/2019 | Sunderland AFC U23 | - | Aston Villa U23 | 1:2 |  |
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| 5. Round | 16/09/2019 | Sunderland AFC U23 | - | Middlesbrough FC U23 | 2:3 | ||||
| 6. Round | 22/09/2019 | Swansea City U23 | - | Sunderland AFC U23 | 1:0 |  |
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| 8. Round | 21/10/2019 | Sunderland AFC U23 | - | Newcastle United U23 | 0:2 | ||||
| 9. Round | 25/10/2019 | Fulham FC U23 | - | Sunderland AFC U23 | 4:0 | ||||
| 10. Round | 03/11/2019 | Sunderland AFC U23 | - | Reading FC U23 | 0:4 | ||||
| 11. Round | 22/11/2019 | Manchester United U23 | - | Sunderland AFC U23 | 3:0 | ||||
| 12. Round | 09/12/2019 | Sunderland AFC U23 | - | Stoke City U23 | 0:1 | ||||
| 14. Round | 06/01/2020 | Aston Villa U23 | - | Sunderland AFC U23 | 4:0 | ||||
| 15. Round | 13/01/2020 | Sunderland AFC U23 | - | West Bromwich Albion U23 | 0:4 | ||||
| 16. Round | 02/02/2020 | Sunderland AFC U23 | - | West Ham United U23 | 2:4 | ||||
| 17. Round | 14/02/2020 | Newcastle United U23 | - | Sunderland AFC U23 | 2:0 | ||||
| 18. Round | 01/03/2020 | Sunderland AFC U23 | - | Fulham FC U23 | 0:3 |
Scotland