| 1. Round | 10/08/2019 | Liverpool FC U23 | - | Tottenham Hotspur U23 | 0:4 | ||||
| 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 |  |
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| 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 | ||||
| 7. Round | 27/09/2019 | Brighton & Hove Albion U23 | - | Tottenham Hotspur U23 | 4:1 | |
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| 8. Round | 18/10/2019 | Tottenham Hotspur U23 | - | Leicester City U23 | 0:2 | ||||
| 11. Round | 22/11/2019 | Everton FC U23 | - | Tottenham Hotspur U23 | 1:3 |  |
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| 12. Round | 06/12/2019 | Tottenham Hotspur U23 | - | Liverpool FC U23 | 4:0 | |
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| 13. Round | 15/12/2019 | Manchester City U23 | - | Tottenham Hotspur U23 | 2:0 | ||||
| 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 | ||||
| 17. Round | 14/02/2020 | Leicester City U23 | - | Tottenham Hotspur U23 | 3:2 | ||||
| 18. Round | 02/03/2020 | Tottenham Hotspur U23 | - | Wolverhampton Wanderers U23 | 3:2 |
England