| 1. Round | 15/08/2016 | Tottenham Hotspur U23 | - | Everton FC U23 | 0:2 | ||||
| 2. Round | 22/08/2016 | Reading FC U23 | - | Tottenham Hotspur U23 | 1:4 |  |
 |
||
| 3. Round | 26/08/2016 | Derby County U23 | - | Tottenham Hotspur U23 | 1:2 | |
|||
| 4. Round | 09/09/2016 | Chelsea FC U23 | - | Tottenham Hotspur U23 | 3:1 | |
|||
| 7. Round | 14/10/2016 | Tottenham Hotspur U23 | - | Manchester City U23 | 1:2 | |
|||
| 9. Round | 28/10/2016 | Tottenham Hotspur U23 | - | Manchester United U23 | 1:1 | |
|||
| 10. Round | 18/11/2016 | Tottenham Hotspur U23 | - | Arsenal FC U23 | 0:2 | ||||
| 11. Round | 28/11/2016 | Sunderland AFC U23 | - | Tottenham Hotspur U23 | 2:2 | ||||
| 12. Round | 12/12/2016 | Tottenham Hotspur U23 | - | Derby County U23 | 2:0 | |
|||
| 14. Round | 06/01/2017 | Tottenham Hotspur U23 | - | Chelsea FC U23 | 2:2 | |
|||
| 15. Round | 13/01/2017 | Manchester City U23 | - | Tottenham Hotspur U23 | 2:2 | ||||
| 18. Round | 20/02/2017 | Tottenham Hotspur U23 | - | Sunderland AFC U23 | 1:0 | ||||
| 22. Round | 15/05/2017 | Manchester United U23 | - | Tottenham Hotspur U23 | 3:2 |
England
Jamaica