| 8. Round | 19/10/2018 | Tottenham Hotspur U23 | - | Leicester City U23 | 1:0 | ||||
| 10. Round | 02/11/2018 | Tottenham Hotspur U23 | - | Swansea City U23 | 1:4 | ||||
| 11. Round | 23/11/2018 | Chelsea FC U23 | - | Tottenham Hotspur U23 | 1:1 | ||||
| 12. Round | 07/12/2018 | Tottenham Hotspur U23 | - | Everton FC U23 | 2:2 |  |
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| 13. Round | 15/12/2018 | Manchester City U23 | - | Tottenham Hotspur U23 | 1:2 | |
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| 14. Round | 07/01/2019 | Tottenham Hotspur U23 | - | Liverpool FC U23 | 1:1 | |
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| 15. Round | 13/01/2019 | West Ham United U23 | - | Tottenham Hotspur U23 | 1:1 |
England
Jamaica