| 1. Round | 10/08/2019 | Fulham FC [U18] | - | Tottenham Hotspur [U18] | 4:0 | ||||
| 2. Round | 17/08/2019 | Tottenham Hotspur [U18] | - | Brighton & Hove Albion [U18] | 2:3 | ||||
| 3. Round | 24/08/2019 | Tottenham Hotspur [U18] | - | Norwich City [U18] | 4:0 |  |
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| 4. Round | 31/08/2019 | Swansea City [U18] | - | Tottenham Hotspur [U18] | 0:4 | |
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| 5. Round | 14/09/2019 | Tottenham Hotspur [U18] | - | West Ham United [U18] | 2:3 | |
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| 6. Round | 21/09/2019 | Southampton FC [U18] | - | Tottenham Hotspur [U18] | 0:2 | ||||
| 7. Round | 05/10/2019 | Tottenham Hotspur [U18] | - | Aston Villa [U18] | 2:4 | ||||
| 9. Round | 09/11/2019 | Tottenham Hotspur [U18] | - | Chelsea FC [U18] | 3:5 | ||||
| 11. Round | 07/12/2019 | Tottenham Hotspur [U18] | - | Reading FC [U18] | 2:3 | ||||
| 17. Round | 29/02/2020 | Tottenham Hotspur [U18] | - | Southampton FC [U18] | 6:1 | |
England