| 4. Round | 30/08/2019 | Chelsea FC U23 | - | Tottenham Hotspur U23 | 2:2 | ||||
| 5. Round | 13/09/2019 | Chelsea FC U23 | - | Brighton & Hove Albion U23 | 2:1 |  |
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| 6. Round | 21/09/2019 | Southampton FC U23 | - | Chelsea FC U23 | 0:2 | ||||
| 7. Round | 28/09/2019 | Leicester City U23 | - | Chelsea FC U23 | 2:2 | ||||
| 8. Round | 18/10/2019 | Chelsea FC U23 | - | Arsenal FC U23 | 3:1 | ||||
| 10. Round | 02/11/2019 | Chelsea FC U23 | - | Blackburn Rovers U23 | 2:1 | ||||
| 12. Round | 07/12/2019 | Chelsea FC U23 | - | Derby County U23 | 3:3 | ||||
| 13. Round | 14/12/2019 | Liverpool FC U23 | - | Chelsea FC U23 | 1:1 | |
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| 14. Round | 06/01/2020 | Tottenham Hotspur U23 | - | Chelsea FC U23 | 0:1 | ||||
| 15. Round | 11/01/2020 | Chelsea FC U23 | - | Manchester City U23 | 2:1 | ||||
| 9. Round | 24/01/2020 | Everton FC U23 | - | Chelsea FC U23 | 2:2 | ||||
| 16. Round | 31/01/2020 | Chelsea FC U23 | - | Leicester City U23 | 2:2 | |
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| 17. Round | 17/02/2020 | Arsenal FC U23 | - | Chelsea FC U23 | 1:2 | ||||
| 18. Round | 02/03/2020 | Chelsea FC U23 | - | Everton FC U23 | 1:0 |
England