| 1. Round | 11/08/2023 | Chelsea FC U21 | - | Blackburn Rovers U21 | 6:1 | ||||
| 2. Round | 18/08/2023 | Chelsea FC U21 | - | Brighton & Hove Albion U21 | 2:3 |  |
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| 3. Round | 25/08/2023 | Norwich City U21 | - | Chelsea FC U21 | 3:2 | ||||
| 4. Round | 01/09/2023 | Chelsea FC U21 | - | West Bromwich Albion U21 | 3:0 | ||||
| 6. Round | 02/10/2023 | Tottenham Hotspur U21 | - | Chelsea FC U21 | 4:2 | ||||
| 7. Round | 27/10/2023 | Chelsea FC U21 | - | Leicester City U21 | 1:1 | ||||
| 10. Round | 17/12/2023 | Liverpool FC U21 | - | Chelsea FC U21 | 2:1 | ||||
| 11. Round | 12/01/2024 | Chelsea FC U21 | - | Manchester United U21 | 3:2 | |
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| 12. Round | 27/01/2024 | Chelsea FC U21 | - | Reading FC U21 | 3:2 | ||||
| 13. Round | 09/02/2024 | West Ham United U21 | - | Chelsea FC U21 | 0:2 | ||||
| 14. Round | 19/02/2024 | Leeds United U21 | - | Chelsea FC U21 | 0:2 | ||||
| 15. Round | 01/03/2024 | Chelsea FC U21 | - | Arsenal FC U21 | 2:4 | |
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| 16. Round | 08/03/2024 | Newcastle United U21 | - | Chelsea FC U21 | 1:7 | ||||
| 17. Round | 15/03/2024 | Chelsea FC U21 | - | Nottingham Forest U21 | 2:3 | ||||
| 18. Round | 08/04/2024 | Aston Villa U21 | - | Chelsea FC U21 | 0:4 | ||||
| 19. Round | 12/04/2024 | Crystal Palace U21 | - | Chelsea FC U21 | 2:2 |
England