| 7. Ronde | 27.10.2023 | West Ham United U21 | - | Middlesbrough FC U21 | 5:0 | ||||
| 8. Ronde | 05.11.2023 | Middlesbrough FC U21 | - | Derby County U21 | 1:0 | ||||
| 11. Ronde | 12.01.2024 | Arsenal FC U21 | - | Middlesbrough FC U21 | 1:0 |  |
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| 12. Ronde | 26.01.2024 | Middlesbrough FC U21 | - | West Bromwich Albion U21 | 0:1 | ||||
| 16. Ronde | 08.03.2024 | Middlesbrough FC U21 | - | Manchester United U21 | 3:2 | ||||
| 17. Ronde | 17.03.2024 | Middlesbrough FC U21 | - | Tottenham Hotspur U21 | 1:2 | ||||
| 13. Ronde | 22.03.2024 | Middlesbrough FC U21 | - | Newcastle United U21 | 3:2 | ||||
| 18. Ronde | 08.04.2024 | Fulham FC U21 | - | Middlesbrough FC U21 | 2:2 | ||||
| 19. Ronde | 15.04.2024 | Sunderland AFC U21 | - | Middlesbrough FC U21 | 1:2 | |
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| 20. Ronde | 26.04.2024 | Middlesbrough FC U21 | - | Crystal Palace U21 | 2:3 |
Engeland