| 1. Round | 11/08/2019 | Manchester City U23 | - | Southampton FC U23 | 3:4 | ||||
| 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 |  |
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| 16. Round | 03/02/2020 | Southampton FC U23 | - | Wolverhampton Wanderers U23 | 1:0 | ||||
| 17. Round | 14/02/2020 | Blackburn Rovers U23 | - | Southampton FC U23 | 2:2 |  |
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| 18. Round | 02/03/2020 | Southampton FC U23 | - | Leicester City U23 | 1:3 |
England