| 1. Round | 12/08/2019 | Stoke City U23 | - | Sunderland AFC U23 | 1:1 |  |
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| 2. Round | 18/08/2019 | Sunderland AFC U23 | - | Norwich City U23 | 1:2 |  |
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| 3. Round | 23/08/2019 | West Bromwich Albion U23 | - | Sunderland AFC U23 | 6:0 | ||||
| 4. Round | 30/08/2019 | Sunderland AFC U23 | - | Aston Villa U23 | 1:2 | ||||
| 5. Round | 16/09/2019 | Sunderland AFC U23 | - | Middlesbrough FC U23 | 2:3 | |
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| 6. Round | 22/09/2019 | Swansea City U23 | - | Sunderland AFC U23 | 1:0 | ||||
| 7. Round | 29/09/2019 | West Ham United U23 | - | Sunderland AFC U23 | 4:2 | ||||
| 15. Round | 13/01/2020 | Sunderland AFC U23 | - | West Bromwich Albion U23 | 0:4 | |
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| 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 | |
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| 18. Round | 01/03/2020 | Sunderland AFC U23 | - | Fulham FC U23 | 0:3 |
England