| 1. Round | 11/08/2018 | Tottenham Hotspur [U18] | - | Brighton & Hove Albion [U18] | 6:4 |  |
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| 2. Round | 18/08/2018 | Swansea City [U18] | - | Tottenham Hotspur [U18] | 1:5 | |
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| 3. Round | 25/08/2018 | Tottenham Hotspur [U18] | - | Chelsea FC [U18] | 2:0 | ||||
| 5. Round | 15/09/2018 | Tottenham Hotspur [U18] | - | Reading FC [U18] | 1:1 | ||||
| 6. Round | 22/09/2018 | West Ham United [U18] | - | Tottenham Hotspur [U18] | 0:9 | |
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| 8. Round | 20/10/2018 | Tottenham Hotspur [U18] | - | Aston Villa [U18] | 6:1 | ||||
| 10. Round | 24/11/2018 | Tottenham Hotspur [U18] | - | Arsenal FC [U18] | 3:2 | ||||
| 12. Round | 05/01/2019 | Tottenham Hotspur [U18] | - | Swansea City [U18] | 1:0 | ||||
| 13. Round | 12/01/2019 | Brighton & Hove Albion [U18] | - | Tottenham Hotspur [U18] | 1:4 | |
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| 15. Round | 24/03/2019 | Tottenham Hotspur [U18] | - | Southampton FC [U18] | 3:1 | |
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| 21. Round | 02/04/2019 | Arsenal FC [U18] | - | Tottenham Hotspur [U18] | 3:2 | ||||
| 22. Round | 27/04/2019 | Tottenham Hotspur [U18] | - | Leicester City [U18] | 3:4 | |
England