| 1. Ronde | 14.08.2023 | Nottingham Forest U21 | - | Middlesbrough FC U21 | 2:2 | ||||
| 2. Ronde | 18.08.2023 | Middlesbrough FC U21 | - | Everton FC U21 | 2:2 | ||||
| 3. Ronde | 25.08.2023 | Middlesbrough FC U21 | - | Wolverhampton Wanderers U21 | 3:2 |  |
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| 4. Ronde | 03.09.2023 | Liverpool FC U21 | - | Middlesbrough FC U21 | 1:4 | ||||
| 5. Ronde | 25.09.2023 | Leicester City U21 | - | Middlesbrough FC U21 | 1:3 |  |
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| 6. Ronde | 29.09.2023 | Middlesbrough FC U21 | - | Stoke City U21 | 4:1 | |
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| 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 | ||||
| 10. Ronde | 18.12.2023 | Reading FC U21 | - | Middlesbrough FC U21 | 2:2 | ||||
| 11. Ronde | 12.01.2024 | Arsenal FC U21 | - | Middlesbrough FC U21 | 1:0 | ||||
| 12. Ronde | 26.01.2024 | Middlesbrough FC U21 | - | West Bromwich Albion U21 | 0:1 | |
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| 9. Ronde | 23.02.2024 | Middlesbrough FC U21 | - | Chelsea FC U21 | 1:3 | ||||
| 15. Ronde | 01.03.2024 | Norwich City U21 | - | Middlesbrough FC U21 | 2:3 | ||||
| 18. Ronde | 08.04.2024 | Fulham FC U21 | - | Middlesbrough FC U21 | 2:2 | ||||
| 20. Ronde | 26.04.2024 | Middlesbrough FC U21 | - | Crystal Palace U21 | 2:3 |
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