| 1. Round | 12/08/2019 | Reading FC U23 | - | Newcastle United U23 | 6:0 |  |
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| 2. Round | 16/08/2019 | Manchester United U23 | - | Reading FC U23 | 2:0 | ||||
| 3. Round | 23/08/2019 | West Ham United U23 | - | Reading FC U23 | 3:0 | ||||
| 4. Round | 02/09/2019 | Reading FC U23 | - | West Bromwich Albion U23 | 2:1 | |
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| 5. Round | 16/09/2019 | Reading FC U23 | - | Swansea City U23 | 5:0 | |
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| 6. Round | 20/09/2019 | Fulham FC U23 | - | Reading FC U23 | 5:4 | ||||
| 7. Round | 30/09/2019 | Reading FC U23 | - | Stoke City U23 | 0:4 | ||||
| 8. Round | 18/10/2019 | Middlesbrough FC U23 | - | Reading FC U23 | 2:1 | ||||
| 9. Round | 28/10/2019 | Reading FC U23 | - | Aston Villa U23 | 3:3 | ||||
| 10. Round | 03/11/2019 | Sunderland AFC U23 | - | Reading FC U23 | 0:4 | ||||
| 11. Round | 25/11/2019 | Reading FC U23 | - | Norwich City U23 | 0:1 | ||||
| 13. Round | 16/12/2019 | Reading FC U23 | - | Manchester United U23 | 1:4 | ||||
| 14. Round | 06/01/2020 | West Bromwich Albion U23 | - | Reading FC U23 | 4:2 | |
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| 15. Round | 13/01/2020 | Reading FC U23 | - | West Ham United U23 | 3:3 | |
England
Jamaica