| 1. Round | 11/08/2019 | Manchester City U23 | - | Southampton FC U23 | 3:4 | ||||
| 2. Round | 19/08/2019 | Southampton FC U23 | - | Derby County U23 | 0:1 | ||||
| 3. Round | 26/08/2019 | Southampton FC U23 | - | Liverpool FC U23 | 2:4 | ||||
| 4. Round | 30/08/2019 | Everton FC U23 | - | Southampton FC U23 | 8:2 |  |
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| 5. Round | 13/09/2019 | Tottenham Hotspur U23 | - | Southampton FC U23 | 2:2 | ||||
| 6. Round | 21/09/2019 | Southampton FC U23 | - | Chelsea FC U23 | 0:2 | |
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| 7. Round | 27/09/2019 | Wolverhampton Wanderers U23 | - | Southampton FC U23 | 1:2 | ||||
| 9. Round | 25/10/2019 | Leicester City U23 | - | Southampton FC U23 | 3:0 | ||||
| 13. Round | 16/12/2019 | Derby County U23 | - | Southampton FC U23 | 4:2 | ||||
| 18. Round | 02/03/2020 | Southampton FC U23 | - | Leicester City U23 | 1:3 |
England