| 4. Round | 01/09/2018 | Fulham FC U23 | - | Southampton FC U23 | 1:1 | ||||
| 5. Round | 14/09/2018 | Newcastle United U23 | - | Southampton FC U23 | 0:1 | ||||
| 6. Round | 21/09/2018 | Southampton FC U23 | - | Aston Villa U23 | 0:1 | ||||
| 7. Round | 29/09/2018 | Reading FC U23 | - | Southampton FC U23 | 2:0 | ||||
| 9. Round | 28/10/2018 | Sunderland AFC U23 | - | Southampton FC U23 | 0:2 | ||||
| 10. Round | 02/11/2018 | Southampton FC U23 | - | West Bromwich Albion U23 | 1:0 |  |
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| 11. Round | 23/11/2018 | Norwich City U23 | - | Southampton FC U23 | 0:0 | ||||
| 12. Round | 07/12/2018 | Aston Villa U23 | - | Southampton FC U23 | 2:1 | ||||
| 13. Round | 14/12/2018 | Southampton FC U23 | - | Newcastle United U23 | 2:1 |  |
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| 14. Round | 04/01/2019 | Southampton FC U23 | - | Stoke City U23 | 2:0 | |
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| 15. Round | 13/01/2019 | Middlesbrough FC U23 | - | Southampton FC U23 | 1:2 | |
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| 16. Round | 01/02/2019 | Manchester United U23 | - | Southampton FC U23 | 0:1 | |
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| 17. Round | 15/02/2019 | Southampton FC U23 | - | Fulham FC U23 | 2:1 | |
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| 18. Round | 01/03/2019 | Southampton FC U23 | - | Reading FC U23 | 1:2 |
Ireland
Nigeria