| 1. Round | 10/08/2019 | Liverpool FC U23 | - | Tottenham Hotspur U23 | 0:4 | ||||
| 2. Round | 16/08/2019 | Tottenham Hotspur U23 | - | Manchester City U23 | 3:1 | ||||
| 6. Round | 23/09/2019 | Blackburn Rovers U23 | - | Tottenham Hotspur U23 | 4:0 | ||||
| 14. Round | 06/01/2020 | Tottenham Hotspur U23 | - | Chelsea FC U23 | 0:1 |  |
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| 15. Round | 13/01/2020 | Derby County U23 | - | Tottenham Hotspur U23 | 2:2 |
England
USA