| 7. Round | 06/10/2018 | Swansea City [U18] | - | Southampton FC [U18] | 1:3 |  |
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| 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 | ||||
| 11. Round | 01/12/2018 | Southampton FC [U18] | - | Norwich City [U18] | 4:1 | ||||
| 12. Round | 05/01/2019 | Southampton FC [U18] | - | West Ham United [U18] | 5:1 |  |
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| 13. Round | 12/01/2019 | Chelsea FC [U18] | - | Southampton FC [U18] | 2:2 | ||||
| 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 | ||||
| 15. Round | 24/03/2019 | Tottenham Hotspur [U18] | - | Southampton FC [U18] | 3:1 | ||||
| 19. Round | 30/03/2019 | Southampton FC [U18] | - | Reading FC [U18] | 2:0 | ||||
| 20. Round | 06/04/2019 | Leicester City [U18] | - | Southampton FC [U18] | 3:4 | ||||
| 21. Round | 13/04/2019 | Southampton FC [U18] | - | Aston Villa [U18] | 1:3 | ||||
| 22. Round | 27/04/2019 | Norwich City [U18] | - | Southampton FC [U18] | 1:4 | |
Ireland
Nigeria