| 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 | ||||
| 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 | ||||
| 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 | ||||
| 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 | ||||
| 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 | ||||
| 17. Round | 14/02/2020 | Blackburn Rovers U23 | - | Southampton FC U23 | 2:2 |  |
|||
| 18. Round | 02/03/2020 | Southampton FC U23 | - | Leicester City U23 | 1:3 |
Ireland