| 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 | ||||
| 12. Round | 27/01/2024 | Chelsea FC U21 | - | Reading FC U21 | 3:2 | ||||
| 15. Round | 01/03/2024 | Chelsea FC U21 | - | Arsenal FC U21 | 2:4 | ||||
| 17. Round | 15/03/2024 | Chelsea FC U21 | - | Nottingham Forest U21 | 2:3 | ||||
| 20. Round | 26/04/2024 | Chelsea FC U21 | - | Southampton FC U21 | 2:0 |
England