| 2. Journée | 18.08.2023 | Middlesbrough FC U21 | - | Everton FC U21 | 2:2 | ||||
| 3. Journée | 25.08.2023 | Middlesbrough FC U21 | - | Wolverhampton Wanderers U21 | 3:2 |  |
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| 4. Journée | 03.09.2023 | Liverpool FC U21 | - | Middlesbrough FC U21 | 1:4 | |
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| 5. Journée | 25.09.2023 | Leicester City U21 | - | Middlesbrough FC U21 | 1:3 | |
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| 6. Journée | 29.09.2023 | Middlesbrough FC U21 | - | Stoke City U21 | 4:1 | |
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| 7. Journée | 27.10.2023 | West Ham United U21 | - | Middlesbrough FC U21 | 5:0 | ||||
| 8. Journée | 05.11.2023 | Middlesbrough FC U21 | - | Derby County U21 | 1:0 | |
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| 12. Journée | 26.01.2024 | Middlesbrough FC U21 | - | West Bromwich Albion U21 | 0:1 |
Irlande