| 8. Round | 19/10/2018 | Tottenham Hotspur U23 | - | Leicester City U23 | 1:0 |  |
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| 9. Round | 28/10/2018 | Derby County U23 | - | Tottenham Hotspur 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 | |
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| 13. Round | 15/12/2018 | Manchester City U23 | - | Tottenham Hotspur U23 | 1:2 | ||||
| 15. Round | 13/01/2019 | West Ham United U23 | - | Tottenham Hotspur U23 | 1:1 | ||||
| 21. Round | 15/04/2019 | Swansea City U23 | - | Tottenham Hotspur U23 | 1:2 | ||||
| 22. Round | 29/04/2019 | Tottenham Hotspur U23 | - | Derby County U23 | 3:1 |
England
Ireland