| 1. Round | 09/08/2019 | Middlesbrough FC U23 | - | Aston Villa U23 | 1:0 | ||||
| 2. Round | 19/08/2019 | Swansea City U23 | - | Aston Villa U23 | 1:1 | ||||
| 3. Round | 24/08/2019 | Aston Villa U23 | - | Norwich City U23 | 1:1 | ||||
| 4. Round | 30/08/2019 | Sunderland AFC U23 | - | Aston Villa U23 | 1:2 | ||||
| 5. Round | 16/09/2019 | Stoke City U23 | - | Aston Villa U23 | 2:0 | ||||
| 6. Round | 23/09/2019 | Aston Villa U23 | - | Manchester United U23 | 4:1 |  |
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| 8. Round | 21/10/2019 | Aston Villa U23 | - | Fulham FC U23 | 1:0 | |
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| 9. Round | 28/10/2019 | Reading FC U23 | - | Aston Villa U23 | 3:3 | ||||
| 10. Round | 04/11/2019 | Aston Villa U23 | - | Newcastle United U23 | 3:2 | ||||
| 11. Round | 22/11/2019 | West Ham United U23 | - | Aston Villa U23 | 4:0 | ||||
| 12. Round | 09/12/2019 | Aston Villa U23 | - | Middlesbrough FC U23 | 5:3 | |
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| 13. Round | 16/12/2019 | Aston Villa U23 | - | Swansea City U23 | 1:1 | ||||
| 14. Round | 06/01/2020 | Aston Villa U23 | - | Sunderland AFC U23 | 4:0 | |
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| 16. Round | 03/02/2020 | Aston Villa U23 | - | West Bromwich Albion U23 | 0:1 |
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