| 2. Round | 18/09/2020 | Southampton FC U23 | - | Chelsea FC U23 | 1:4 | ||||
| 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 | ||||
| 7. Round | 04/12/2020 | Chelsea FC U23 | - | Leicester City U23 | 2:1 | ||||
| 12. Round | 18/12/2020 | Chelsea FC U23 | - | Manchester United U23 | 6:1 | ||||
| 25. Round | 23/04/2021 | Manchester United U23 | - | Chelsea FC U23 | 4:2 |  |
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| 13. Round | 07/05/2021 | Blackburn Rovers U23 | - | Chelsea FC U23 | 2:4 |
Finland