| 1. Round | 11/08/2023 | Chelsea FC U21 | - | Blackburn Rovers U21 | 6:1 |  |
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| 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 | |
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| 4. Round | 01/09/2023 | Chelsea FC U21 | - | West Bromwich Albion U21 | 3:0 | ||||
| 5. Round | 22/09/2023 | Manchester City U21 | - | Chelsea FC U21 | 1:2 | ||||
| 6. Round | 02/10/2023 | Tottenham Hotspur U21 | - | Chelsea FC U21 | 4:2 | |
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| 7. Round | 27/10/2023 | Chelsea FC U21 | - | Leicester City U21 | 1:1 | ||||
| 8. Round | 03/11/2023 | Chelsea FC U21 | - | Fulham FC U21 | 2:2 | ||||
| 13. Round | 09/02/2024 | West Ham United U21 | - | Chelsea FC U21 | 0:2 | |
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| 14. Round | 19/02/2024 | Leeds United U21 | - | Chelsea FC U21 | 0:2 | |
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| 9. Round | 23/02/2024 | Middlesbrough FC U21 | - | Chelsea FC U21 | 1:3 | |
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| 15. Round | 01/03/2024 | Chelsea FC U21 | - | Arsenal FC U21 | 2:4 | ||||
| 16. Round | 08/03/2024 | Newcastle United U21 | - | Chelsea FC U21 | 1:7 | |
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| 17. Round | 15/03/2024 | Chelsea FC U21 | - | Nottingham Forest U21 | 2:3 | |
England