| 5. Ronde | 25.09.2023 | Leicester City U21 | - | Middlesbrough FC U21 | 1:3 | ||||
| 6. Ronde | 29.09.2023 | Middlesbrough FC U21 | - | Stoke City U21 | 4:1 | ||||
| 10. Ronde | 18.12.2023 | Reading FC U21 | - | Middlesbrough FC U21 | 2:2 |  |
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| 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 | |
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| 14. Ronde | 16.02.2024 | Aston Villa U21 | - | Middlesbrough FC U21 | 4:0 | ||||
| 9. Ronde | 23.02.2024 | Middlesbrough FC U21 | - | Chelsea FC U21 | 1:3 | ||||
| 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 | |
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| 18. Ronde | 08.04.2024 | Fulham FC U21 | - | Middlesbrough FC U21 | 2:2 | |
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| 20. Ronde | 26.04.2024 | Middlesbrough FC U21 | - | Crystal Palace U21 | 2:3 |
Engeland