| 1. Round | 12/09/2020 | Tottenham Hotspur U23 | - | Brighton & Hove Albion U23 | 1:1 | ||||
| 2. Round | 18/09/2020 | Tottenham Hotspur U23 | - | West Ham United U23 | 3:0 |  |
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| 9. Round | 22/11/2020 | Manchester United U23 | - | Tottenham Hotspur U23 | 4:2 | ||||
| 7. Round | 07/12/2020 | Blackburn Rovers U23 | - | Tottenham Hotspur U23 | 2:3 |  |
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| 11. Round | 14/12/2020 | Chelsea FC U23 | - | Tottenham Hotspur U23 | 3:2 | ||||
| 12. Round | 19/12/2020 | Liverpool FC U23 | - | Tottenham Hotspur U23 | 3:4 | |
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| 14. Round | 15/01/2021 | Brighton & Hove Albion U23 | - | Tottenham Hotspur U23 | 1:5 | |
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| 15. Round | 22/01/2021 | West Ham United U23 | - | Tottenham Hotspur U23 | 1:2 | |
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| 16. Round | 29/01/2021 | Tottenham Hotspur U23 | - | Arsenal FC U23 | 1:1 | ||||
| 17. Round | 07/02/2021 | Southampton FC U23 | - | Tottenham Hotspur U23 | 1:1 | ||||
| 20. Round | 26/02/2021 | Tottenham Hotspur U23 | - | Blackburn Rovers U23 | 1:1 | ||||
| 18. Round | 05/03/2021 | Tottenham Hotspur U23 | - | Everton FC U23 | 2:1 | ||||
| 21. Round | 15/03/2021 | Derby County U23 | - | Tottenham Hotspur U23 | 1:0 | ||||
| 22. Round | 19/03/2021 | Tottenham Hotspur U23 | - | Manchester United U23 | 3:0 | |
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England