| 1. Round | 16/08/2021 | Tottenham Hotspur U23 | - | Chelsea FC U23 | 2:2 | ||||
| 2. Round | 20/08/2021 | Chelsea FC U23 | - | Manchester United U23 | 1:1 | ||||
| 3. Round | 29/08/2021 | West Ham United U23 | - | Chelsea FC U23 | 2:1 | ||||
| 4. Round | 11/09/2021 | Manchester City U23 | - | Chelsea FC U23 | 4:1 | ||||
| 6. Round | 24/09/2021 | Chelsea FC U23 | - | Liverpool FC U23 | 4:3 |  |
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| 7. Round | 03/10/2021 | Chelsea FC U23 | - | Blackburn Rovers U23 | 0:1 | ||||
| 8. Round | 16/10/2021 | Chelsea FC U23 | - | Derby County U23 | 2:0 | ||||
| 9. Round | 23/10/2021 | Leicester City U23 | - | Chelsea FC U23 | 1:1 | ||||
| 10. Round | 30/10/2021 | Chelsea FC U23 | - | Everton FC U23 | 1:1 | ||||
| 14. Round | 03/12/2021 | Derby County U23 | - | Chelsea FC U23 | 3:1 | ||||
| 16. Round | 08/01/2022 | Chelsea FC U23 | - | Leicester City U23 | 5:0 | ||||
| 17. Round | 17/01/2022 | Crystal Palace U23 | - | Chelsea FC U23 | 3:2 | |
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| 18. Round | 24/01/2022 | Chelsea FC U23 | - | Manchester City U23 | 0:1 | ||||
| 19. Round | 04/02/2022 | Arsenal FC U23 | - | Chelsea FC U23 | 3:1 | ||||
| 23. Round | 20/03/2022 | Chelsea FC U23 | - | Leeds United U23 | 1:0 | |
England