| 1. Round | 12/08/2019 | Reading FC U23 | - | Newcastle United U23 | 6:0 | ||||
| 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 |  |
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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 | ||||
| 13. Round | 16/12/2019 | Reading FC U23 | - | Manchester United U23 | 1:4 | ||||
| 15. Round | 13/01/2020 | Reading FC U23 | - | West Ham United U23 | 3:3 | ||||
| 17. Round | 17/02/2020 | Reading FC U23 | - | Middlesbrough FC U23 | 0:1 |
Iceland