| 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 |  |
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| 3. Ronde | 25.08.2023 | Middlesbrough FC U21 | - | Wolverhampton Wanderers U21 | 3:2 | ||||
| 4. Ronde | 03.09.2023 | Liverpool FC U21 | - | Middlesbrough FC U21 | 1:4 | |
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| 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 | ||||
| 7. Ronde | 27.10.2023 | West Ham United U21 | - | Middlesbrough FC U21 | 5:0 | ||||
| 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 |
Engeland