| 1. Round | 10/08/2019 | Liverpool FC U23 | - | Tottenham Hotspur U23 | 0:4 |  |
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| 2. Round | 16/08/2019 | Tottenham Hotspur U23 | - | Manchester City U23 | 3:1 | ||||
| 3. Round | 23/08/2019 | Tottenham Hotspur U23 | - | Derby County U23 | 1:2 | ||||
| 4. Round | 30/08/2019 | Chelsea FC U23 | - | Tottenham Hotspur U23 | 2:2 | ||||
| 5. Round | 13/09/2019 | Tottenham Hotspur U23 | - | Southampton FC U23 | 2:2 | ||||
| 6. Round | 23/09/2019 | Blackburn Rovers U23 | - | Tottenham Hotspur U23 | 4:0 |  |
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| 7. Round | 27/09/2019 | Brighton & Hove Albion U23 | - | Tottenham Hotspur U23 | 4:1 | ||||
| 8. Round | 18/10/2019 | Tottenham Hotspur U23 | - | Leicester City U23 | 0:2 | ||||
| 9. Round | 26/10/2019 | Wolverhampton Wanderers U23 | - | Tottenham Hotspur U23 | 1:2 | ||||
| 10. Round | 01/11/2019 | Tottenham Hotspur U23 | - | Arsenal FC U23 | 1:3 | ||||
| 11. Round | 22/11/2019 | Everton FC U23 | - | Tottenham Hotspur U23 | 1:3 | ||||
| 14. Round | 06/01/2020 | Tottenham Hotspur U23 | - | Chelsea FC U23 | 0:1 | ||||
| 15. Round | 13/01/2020 | Derby County U23 | - | Tottenham Hotspur U23 | 2:2 |
England