| 3. Round | 23/08/2019 | Arsenal FC U23 | - | Everton FC U23 | 2:2 | ||||
| 4. Round | 30/08/2019 | Derby County U23 | - | Arsenal FC U23 | 2:2 | ||||
| 5. Round | 14/09/2019 | Arsenal FC U23 | - | Leicester City U23 | 2:1 | ||||
| 6. Round | 20/09/2019 | Wolverhampton Wanderers U23 | - | Arsenal FC U23 | 2:2 | ||||
| 8. Round | 18/10/2019 | Chelsea FC U23 | - | Arsenal FC U23 | 3:1 | ||||
| 9. Round | 26/10/2019 | Manchester City U23 | - | Arsenal FC U23 | 1:1 | ||||
| 10. Round | 01/11/2019 | Tottenham Hotspur U23 | - | Arsenal FC U23 | 1:3 | ||||
| 11. Round | 23/11/2019 | Arsenal FC U23 | - | Southampton FC U23 | 1:0 | ||||
| 14. Round | 03/01/2020 | Arsenal FC U23 | - | Derby County U23 | 2:2 | ||||
| 16. Round | 01/02/2020 | Liverpool FC U23 | - | Arsenal FC U23 | 3:0 | ||||
| 17. Round | 17/02/2020 | Arsenal FC U23 | - | Chelsea FC U23 | 1:2 |
Estonia