| 3. Round | 25/08/2018 | Fulham FC [U18] | - | Southampton FC [U18] | 2:2 | ||||
| 5. Round | 15/09/2018 | Arsenal FC [U18] | - | Southampton FC [U18] | 1:0 | ||||
| 6. Round | 22/09/2018 | Southampton FC [U18] | - | Brighton & Hove Albion [U18] | 1:0 | ||||
| 7. Round | 06/10/2018 | Swansea City [U18] | - | Southampton FC [U18] | 1:3 |  |
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| 8. Round | 20/10/2018 | Southampton FC [U18] | - | Leicester City [U18] | 0:1 | ||||
| 9. Round | 03/11/2018 | Reading FC [U18] | - | Southampton FC [U18] | 1:3 | ||||
| 10. Round | 24/11/2018 | Aston Villa [U18] | - | Southampton FC [U18] | 5:1 | ||||
| 13. Round | 12/01/2019 | Chelsea FC [U18] | - | Southampton FC [U18] | 2:2 | |
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| 14. Round | 26/01/2019 | Southampton FC [U18] | - | Fulham FC [U18] | 3:1 | ||||
| 16. Round | 23/02/2019 | Southampton FC [U18] | - | Arsenal FC [U18] | 1:3 | ||||
| 17. Round | 02/03/2019 | Brighton & Hove Albion [U18] | - | Southampton FC [U18] | 1:3 | ||||
| 18. Round | 16/03/2019 | Southampton FC [U18] | - | Swansea City [U18] | 3:0 | ||||
| 21. Round | 13/04/2019 | Southampton FC [U18] | - | Aston Villa [U18] | 1:3 |
Ireland