| 1. Round | 14/09/2020 | Chelsea FC U23 | - | West Ham United U23 | 1:0 | ||||
| 2. Round | 18/09/2020 | Southampton FC U23 | - | Chelsea FC U23 | 1:4 | ||||
| 3. Round | 25/09/2020 | Brighton & Hove Albion U23 | - | Chelsea FC U23 | 2:0 | ||||
| 4. Round | 04/10/2020 | Chelsea FC U23 | - | Arsenal FC U23 | 3:0 | ||||
| 5. Round | 17/10/2020 | Chelsea FC U23 | - | Derby County U23 | 3:2 | ||||
| 6. Round | 24/10/2020 | Liverpool FC U23 | - | Chelsea FC U23 | 3:1 | ||||
| 9. Round | 22/11/2020 | Manchester City U23 | - | Chelsea FC U23 | 2:2 | ||||
| 11. Round | 14/12/2020 | Chelsea FC U23 | - | Tottenham Hotspur U23 | 3:2 |  |
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| 12. Round | 18/12/2020 | Chelsea FC U23 | - | Manchester United U23 | 6:1 | |
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| 17. Round | 05/02/2021 | Arsenal FC U23 | - | Chelsea FC U23 | 2:2 | |
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| 16. Round | 07/03/2021 | Chelsea FC U23 | - | Brighton & Hove Albion U23 | 0:0 | ||||
| 21. Round | 12/03/2021 | Chelsea FC U23 | - | Everton FC U23 | 2:1 | ||||
| 22. Round | 21/03/2021 | Chelsea FC U23 | - | Manchester City U23 | 2:2 | ||||
| 14. Round | 06/04/2021 | West Ham United U23 | - | Chelsea FC U23 | 1:1 | ||||
| 15. Round | 12/04/2021 | Chelsea FC U23 | - | Southampton FC U23 | 3:1 | ||||
| 24. Round | 18/04/2021 | Tottenham Hotspur U23 | - | Chelsea FC U23 | 1:4 |  |
England