| 1. Ronde | 10.08.2019 | Liverpool FC U23 | - | Tottenham Hotspur U23 | 0:4 |  |
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| 2. Ronde | 16.08.2019 | Tottenham Hotspur U23 | - | Manchester City U23 | 3:1 | ||||
| 5. Ronde | 13.09.2019 | Tottenham Hotspur U23 | - | Southampton FC U23 | 2:2 | ||||
| 6. Ronde | 23.09.2019 | Blackburn Rovers U23 | - | Tottenham Hotspur U23 | 4:0 | |
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| 7. Ronde | 27.09.2019 | Brighton & Hove Albion U23 | - | Tottenham Hotspur U23 | 4:1 | ||||
| 10. Ronde | 01.11.2019 | Tottenham Hotspur U23 | - | Arsenal FC U23 | 1:3 | ||||
| 12. Ronde | 06.12.2019 | Tottenham Hotspur U23 | - | Liverpool FC U23 | 4:0 |  |
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| 17. Ronde | 14.02.2020 | Leicester City U23 | - | Tottenham Hotspur U23 | 3:2 | ||||
| 18. Ronde | 02.03.2020 | Tottenham Hotspur U23 | - | Wolverhampton Wanderers U23 | 3:2 | |
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