| 7. Round | 30/09/2023 | Tottenham Hotspur | - | Liverpool FC | 2:1 |  |
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| 8. Round | 07/10/2023 | Luton Town | - | Tottenham Hotspur | 0:1 | ||||
| 9. Round | 23/10/2023 | Tottenham Hotspur | - | Fulham FC | 2:0 | ||||
| 13. Round | 26/11/2023 | Tottenham Hotspur | - | Aston Villa | 1:2 | ||||
| 15. Round | 07/12/2023 | Tottenham Hotspur | - | West Ham United | 1:2 | ||||
| 17. Round | 15/12/2023 | Nottingham Forest | - | Tottenham Hotspur | 0:2 | ||||
| 19. Round | 28/12/2023 | Brighton & Hove Albion | - | Tottenham Hotspur | 4:2 |  |
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| 20. Round | 31/12/2023 | Tottenham Hotspur | - | AFC Bournemouth | 3:1 |
Argentina