| 2. Round | 17/08/2019 | Chelsea FC [U18] | - | West Ham United [U18] | 4:3 | ||||
| 3. Round | 24/08/2019 | West Ham United [U18] | - | Arsenal FC [U18] | 1:1 |  |
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| 4. Round | 31/08/2019 | Reading FC [U18] | - | West Ham United [U18] | 3:3 | ||||
| 5. Round | 14/09/2019 | Tottenham Hotspur [U18] | - | West Ham United [U18] | 2:3 | ||||
| 6. Round | 21/09/2019 | West Ham United [U18] | - | Norwich City [U18] | 4:1 | ||||
| 7. Round | 05/10/2019 | Fulham FC [U18] | - | West Ham United [U18] | 5:1 | ||||
| 8. Round | 19/10/2019 | West Ham United [U18] | - | Brighton & Hove Albion [U18] | 1:1 | ||||
| 10. Round | 30/11/2019 | West Ham United [U18] | - | Aston Villa [U18] | 3:1 |  |
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| 14. Round | 18/01/2020 | West Ham United [U18] | - | Reading FC [U18] | 1:1 | ||||
| 16. Round | 22/02/2020 | West Ham United [U18] | - | Tottenham Hotspur [U18] | 3:1 | ||||
| 20. Round | 07/03/2020 | West Ham United [U18] | - | Leicester City [U18] | 3:2 |
England