| 1. Round | 12/08/2019 | Blackburn Rovers U23 | - | Arsenal FC U23 | 1:3 | ||||
| 2. Round | 16/08/2019 | Arsenal FC U23 | - | Brighton & Hove Albion U23 | 2:1 |  |
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| 3. Round | 23/08/2019 | Arsenal FC U23 | - | Everton FC U23 | 2:2 |  |
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| 4. Round | 30/08/2019 | Derby County U23 | - | Arsenal FC U23 | 2:2 | |
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| 5. Round | 14/09/2019 | Arsenal FC U23 | - | Leicester City U23 | 2:1 | |
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| 6. Round | 20/09/2019 | Wolverhampton Wanderers U23 | - | Arsenal FC U23 | 2:2 | ||||
| 7. Round | 28/09/2019 | Arsenal FC U23 | - | Liverpool FC U23 | 2:2 | |
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| 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 | |
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| 12. Round | 06/12/2019 | Arsenal FC U23 | - | Blackburn Rovers U23 | 3:1 | ||||
| 13. Round | 13/12/2019 | Brighton & Hove Albion U23 | - | Arsenal FC U23 | 1:0 |  |
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| 15. Round | 13/01/2020 | Everton FC U23 | - | Arsenal FC U23 | 3:3 |
England