| 2. Round | 17/08/2019 | Aston Villa [U18] | - | Arsenal FC [U18] | 1:5 | ||||
| 3. Round | 24/08/2019 | West Ham United [U18] | - | Arsenal FC [U18] | 1:1 | ||||
| 4. Round | 31/08/2019 | Arsenal FC [U18] | - | Southampton FC [U18] | 0:1 | ||||
| 5. Round | 14/09/2019 | Leicester City [U18] | - | Arsenal FC [U18] | 1:0 | ||||
| 6. Round | 21/09/2019 | Arsenal FC [U18] | - | Brighton & Hove Albion [U18] | 3:6 | ||||
| 7. Round | 05/10/2019 | Reading FC [U18] | - | Arsenal FC [U18] | 0:1 | ||||
| 8. Round | 19/10/2019 | Arsenal FC [U18] | - | Tottenham Hotspur [U18] | 2:2 | ||||
| 9. Round | 09/11/2019 | Fulham FC [U18] | - | Arsenal FC [U18] | 2:2 | ||||
| 12. Round | 04/01/2020 | Chelsea FC [U18] | - | Arsenal FC [U18] | 2:2 | ||||
| 14. Round | 18/01/2020 | Southampton FC [U18] | - | Arsenal FC [U18] | 0:2 | ||||
| 13. Round | 25/01/2020 | Arsenal FC [U18] | - | Aston Villa [U18] | 1:2 |  |
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| 15. Round | 01/02/2020 | Arsenal FC [U18] | - | West Ham United [U18] | 1:5 | ||||
| 11. Round | 12/02/2020 | Norwich City [U18] | - | Arsenal FC [U18] | 2:2 | ||||
| 16. Round | 22/02/2020 | Arsenal FC [U18] | - | Leicester City [U18] | 2:5 |  |
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| 17. Round | 29/02/2020 | Brighton & Hove Albion [U18] | - | Arsenal FC [U18] | 2:3 | |
Romania