| 4. Round | 16/09/2023 | Southampton FC [U18] | - | Norwich City [U18] | 4:2 |  |
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| 5. Round | 23/09/2023 | Arsenal FC [U18] | - | Southampton FC [U18] | 4:0 | ||||
| 8. Round | 28/10/2023 | Leicester City [U18] | - | Southampton FC [U18] | 2:1 | ||||
| 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 |  |
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| 13. Round | 02/02/2024 | Southampton FC [U18] | - | Tottenham Hotspur [U18] | 3:6 | ||||
| 16. Round | 10/02/2024 | Norwich City [U18] | - | Southampton FC [U18] | 2:3 | |
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| 17. Round | 17/02/2024 | Southampton FC [U18] | - | Arsenal FC [U18] | 2:2 | ||||
| 20. Round | 16/03/2024 | Southampton FC [U18] | - | Leicester City [U18] | 1:1 | ||||
| 21. Round | 06/04/2024 | Aston Villa [U18] | - | Southampton FC [U18] | 0:4 | ||||
| 22. Round | 13/04/2024 | Southampton FC [U18] | - | Crystal Palace [U18] | 0:3 | |
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| 23. Round | 20/04/2024 | Reading FC [U18] | - | Southampton FC [U18] | 0:9 | ||||
| 11. Round | 23/04/2024 | West Bromwich Albion [U18] | - | Southampton FC [U18] | 3:2 |
England