| 1. Round | 12/08/2023 | Crystal Palace [U18] | - | Southampton FC [U18] | 5:0 | ||||
| 2. Round | 19/08/2023 | Southampton FC [U18] | - | Aston Villa [U18] | 0:2 | ||||
| 3. Round | 26/08/2023 | Brighton & Hove Albion [U18] | - | Southampton FC [U18] | 2:2 |  |
|||
| 4. Round | 16/09/2023 | Southampton FC [U18] | - | Norwich City [U18] | 4:2 | |
|||
| 5. Round | 23/09/2023 | Arsenal FC [U18] | - | Southampton FC [U18] | 4:0 | ||||
| 7. Round | 07/10/2023 | Southampton FC [U18] | - | West Ham United [U18] | 2:2 | ||||
| 9. Round | 08/11/2023 | Southampton FC [U18] | - | Reading FC [U18] | 2:1 | ||||
| 10. Round | 19/12/2023 | Chelsea FC [U18] | - | Southampton FC [U18] | 3:2 | ||||
| 14. Round | 13/01/2024 | Fulham FC [U18] | - | Southampton FC [U18] | 3:2 | ||||
| 13. Round | 02/02/2024 | Southampton FC [U18] | - | Tottenham Hotspur [U18] | 3:6 | ||||
| 20. Round | 16/03/2024 | Southampton FC [U18] | - | Leicester City [U18] | 1:1 | ||||
| 15. Round | 07/05/2024 | Southampton FC [U18] | - | Chelsea FC [U18] | 1:2 |
England