| 1. Round | 10/08/2019 | Brighton & Hove Albion [U18] | - | Reading FC [U18] | 3:2 | ||||
| 2. Round | 17/08/2019 | Reading FC [U18] | - | Leicester City [U18] | 1:1 | ||||
| 4. Round | 31/08/2019 | Reading FC [U18] | - | West Ham United [U18] | 3:3 |  |
|||
| 5. Round | 14/09/2019 | Reading FC [U18] | - | Swansea City [U18] | 3:1 | |
|||
| 6. Round | 21/09/2019 | Chelsea FC [U18] | - | Reading FC [U18] | 2:1 | ||||
| 8. Round | 19/10/2019 | Aston Villa [U18] | - | Reading FC [U18] | 1:2 | ||||
| 9. Round | 09/11/2019 | Reading FC [U18] | - | Southampton FC [U18] | 1:2 | ||||
| 10. Round | 30/11/2019 | Reading FC [U18] | - | Norwich City [U18] | 3:5 | |
 |
||
| 11. Round | 07/12/2019 | Tottenham Hotspur [U18] | - | Reading FC [U18] | 2:3 | |
England