| 1. Round | 11/08/2018 | Leicester City [U18] | - | Reading FC [U18] | 1:2 | ||||
| 2. Round | 18/08/2018 | Reading FC [U18] | - | Norwich City [U18] | 1:0 | ||||
| 4. Round | 01/09/2018 | Reading FC [U18] | - | Brighton & Hove Albion [U18] | 3:2 | ||||
| 5. Round | 15/09/2018 | Tottenham Hotspur [U18] | - | Reading FC [U18] | 1:1 | ||||
| 6. Round | 22/09/2018 | Reading FC [U18] | - | Swansea City [U18] | 0:1 | ||||
| 10. Round | 24/11/2018 | Reading FC [U18] | - | West Ham United [U18] | 0:2 | ||||
| 11. Round | 01/12/2018 | Chelsea FC [U18] | - | Reading FC [U18] | 2:0 | ||||
| 12. Round | 05/01/2019 | Norwich City [U18] | - | Reading FC [U18] | 2:1 | ||||
| 14. Round | 19/01/2019 | Reading FC [U18] | - | Aston Villa [U18] | 1:2 | ||||
| 15. Round | 02/02/2019 | Brighton & Hove Albion [U18] | - | Reading FC [U18] | 2:1 | ||||
| 16. Round | 23/02/2019 | Reading FC [U18] | - | Tottenham Hotspur [U18] | 0:2 | ||||
| 17. Round | 02/03/2019 | Swansea City [U18] | - | Reading FC [U18] | 0:1 | ||||
| 22. Round | 27/04/2019 | Reading FC [U18] | - | Chelsea FC [U18] | 0:2 |
England