| 2. Round | 19/08/2023 | Tottenham Hotspur U21 | - | Newcastle United U21 | 4:1 | ||||
| 3. Round | 25/08/2023 | Derby County U21 | - | Tottenham Hotspur U21 | 0:2 | ||||
| 4. Round | 02/09/2023 | Tottenham Hotspur U21 | - | Blackburn Rovers U21 | 4:0 |  |
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| 5. Round | 25/09/2023 | Stoke City U21 | - | Tottenham Hotspur U21 | 0:2 | ||||
| 6. Round | 02/10/2023 | Tottenham Hotspur U21 | - | Chelsea FC U21 | 4:2 | ||||
| 7. Round | 27/10/2023 | Sunderland AFC U21 | - | Tottenham Hotspur U21 | 2:4 | ||||
| 10. Round | 18/12/2023 | Tottenham Hotspur U21 | - | Leeds United U21 | 1:0 |
England