| 2. Round | 19/08/2023 | Chelsea FC [U18] | - | Crystal Palace [U18] | 2:1 | ||||
| 3. Round | 26/08/2023 | Aston Villa [U18] | - | Chelsea FC [U18] | 1:5 | ||||
| 4. Round | 16/09/2023 | Chelsea FC [U18] | - | Fulham FC [U18] | 1:3 | ||||
| 5. Round | 23/09/2023 | Norwich City [U18] | - | Chelsea FC [U18] | 3:6 | ||||
| 7. Round | 07/10/2023 | Brighton & Hove Albion [U18] | - | Chelsea FC [U18] | 0:2 | ||||
| 8. Round | 28/10/2023 | Chelsea FC [U18] | - | Tottenham Hotspur [U18] | 3:4 | ||||
| 10. Round | 19/12/2023 | Chelsea FC [U18] | - | Southampton FC [U18] | 3:2 | ||||
| 13. Round | 06/01/2024 | Leicester City [U18] | - | Chelsea FC [U18] | 2:2 | ||||
| 9. Round | 13/02/2024 | West Ham United [U18] | - | Chelsea FC [U18] | 2:3 | ||||
| 22. Round | 13/04/2024 | West Bromwich Albion [U18] | - | Chelsea FC [U18] | 2:2 | ||||
| 24. Round | 27/04/2024 | Chelsea FC [U18] | - | Leicester City [U18] | 3:2 |  |
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| 25. Round | 04/05/2024 | Chelsea FC [U18] | - | Norwich City [U18] | 1:2 | ||||
| 26. Round | 11/05/2024 | Arsenal FC [U18] | - | Chelsea FC [U18] | 5:2 |
England