| 17. Round | 15/02/2019 | Tottenham Hotspur U23 | - | Arsenal FC U23 | 0:4 | ||||
| 18. Round | 01/03/2019 | Tottenham Hotspur U23 | - | Chelsea FC U23 | 1:1 |  |
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| 19. Round | 08/03/2019 | Leicester City U23 | - | Tottenham Hotspur U23 | 1:2 | ||||
| 20. Round | 08/04/2019 | Tottenham Hotspur U23 | - | Blackburn Rovers U23 | 0:3 | ||||
| 22. Round | 29/04/2019 | Tottenham Hotspur U23 | - | Derby County U23 | 3:1 |
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