| 4. Round | 04/10/2020 | Chelsea FC U23 | - | Arsenal FC U23 | 3:0 | ||||
| 18. Round | 15/02/2021 | Derby County U23 | - | Chelsea FC U23 | 2:1 | ||||
| 19. Round | 19/02/2021 | Chelsea FC U23 | - | Liverpool FC U23 | 2:3 | ||||
| 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 | ||||
| 24. Round | 18/04/2021 | Tottenham Hotspur U23 | - | Chelsea FC U23 | 1:4 | ||||
| 25. Round | 23/04/2021 | Manchester United U23 | - | Chelsea FC U23 | 4:2 | ||||
| 26. Round | 30/04/2021 | Chelsea FC U23 | - | Blackburn Rovers U23 | 1:0 | ||||
| 13. Round | 07/05/2021 | Blackburn Rovers U23 | - | Chelsea FC U23 | 2:4 |  |
England