| 1. Ronde | 11.08.2019 | Manchester City U23 | - | Southampton FC U23 | 3:4 |  |
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| 2. Ronde | 19.08.2019 | Southampton FC U23 | - | Derby County U23 | 0:1 | ||||
| 3. Ronde | 26.08.2019 | Southampton FC U23 | - | Liverpool FC U23 | 2:4 | ||||
| 4. Ronde | 30.08.2019 | Everton FC U23 | - | Southampton FC U23 | 8:2 | ||||
| 5. Ronde | 13.09.2019 | Tottenham Hotspur U23 | - | Southampton FC U23 | 2:2 | ||||
| 6. Ronde | 21.09.2019 | Southampton FC U23 | - | Chelsea FC U23 | 0:2 | ||||
| 7. Ronde | 27.09.2019 | Wolverhampton Wanderers U23 | - | Southampton FC U23 | 1:2 | ||||
| 8. Ronde | 21.10.2019 | Southampton FC U23 | - | Blackburn Rovers U23 | 1:3 |  |
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| 9. Ronde | 25.10.2019 | Leicester City U23 | - | Southampton FC U23 | 3:0 | |
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| 10. Ronde | 01.11.2019 | Southampton FC U23 | - | Brighton & Hove Albion U23 | 1:4 |  |
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| 12. Ronde | 06.12.2019 | Southampton FC U23 | - | Manchester City U23 | 2:0 | |
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| 13. Ronde | 16.12.2019 | Derby County U23 | - | Southampton FC U23 | 4:2 | |
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| 14. Ronde | 06.01.2020 | Southampton FC U23 | - | Everton FC U23 | 1:1 | |
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| 15. Ronde | 13.01.2020 | Liverpool FC U23 | - | Southampton FC U23 | 5:0 |
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