| 1. Ronde | 10.08.2019 | Liverpool FC U23 | - | Tottenham Hotspur U23 | 0:4 | ||||
| 3. Ronde | 23.08.2019 | Tottenham Hotspur U23 | - | Derby County U23 | 1:2 | ||||
| 4. Ronde | 30.08.2019 | Chelsea FC U23 | - | Tottenham Hotspur U23 | 2:2 | ||||
| 5. Ronde | 13.09.2019 | Tottenham Hotspur U23 | - | Southampton FC U23 | 2:2 | ||||
| 8. Ronde | 18.10.2019 | Tottenham Hotspur U23 | - | Leicester City U23 | 0:2 | ||||
| 9. Ronde | 26.10.2019 | Wolverhampton Wanderers U23 | - | Tottenham Hotspur U23 | 1:2 |  |
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| 10. Ronde | 01.11.2019 | Tottenham Hotspur U23 | - | Arsenal FC U23 | 1:3 | ||||
| 11. Ronde | 22.11.2019 | Everton FC U23 | - | Tottenham Hotspur U23 | 1:3 | |
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| 12. Ronde | 06.12.2019 | Tottenham Hotspur U23 | - | Liverpool FC U23 | 4:0 | ||||
| 13. Ronde | 15.12.2019 | Manchester City U23 | - | Tottenham Hotspur U23 | 2:0 | ||||
| 14. Ronde | 06.01.2020 | Tottenham Hotspur U23 | - | Chelsea FC U23 | 0:1 |
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