| 2. Round | 18/08/2023 | Chelsea FC U21 | - | Brighton & Hove Albion U21 | 2:3 | ||||
| 3. Round | 25/08/2023 | Norwich City U21 | - | Chelsea FC U21 | 3:2 | ||||
| 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 | ||||
| 11. Round | 12/01/2024 | Chelsea FC U21 | - | Manchester United U21 | 3:2 | ||||
| 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