| 6. Round | 21/09/2019 | Southampton FC U23 | - | Chelsea FC U23 | 0:2 | ||||
| 7. Round | 27/09/2019 | Wolverhampton Wanderers U23 | - | Southampton FC U23 | 1:2 |  |
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| 8. Round | 21/10/2019 | Southampton FC U23 | - | Blackburn Rovers U23 | 1:3 | ||||
| 10. Round | 01/11/2019 | Southampton FC U23 | - | Brighton & Hove Albion U23 | 1:4 | ||||
| 11. Round | 23/11/2019 | Arsenal FC U23 | - | Southampton FC U23 | 1:0 | ||||
| 12. Round | 06/12/2019 | Southampton FC U23 | - | Manchester City U23 | 2:0 | |
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| 13. Round | 16/12/2019 | Derby County U23 | - | Southampton FC U23 | 4:2 | ||||
| 14. Round | 06/01/2020 | Southampton FC U23 | - | Everton FC U23 | 1:1 | ||||
| 15. Round | 13/01/2020 | Liverpool FC U23 | - | Southampton FC U23 | 5:0 |
England
