| 1. Round | 14/09/2020 | Chelsea FC U23 | - | West Ham United U23 | 1:0 |  |
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| 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 | ||||
| 8. Round | 08/11/2020 | Everton FC U23 | - | Chelsea FC U23 | 2:0 | ||||
| 18. Round | 15/02/2021 | Derby County U23 | - | Chelsea FC U23 | 2:1 | ||||
| 20. Round | 01/03/2021 | Leicester City U23 | - | Chelsea FC U23 | 1:1 | ||||
| 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 | |
Croatia