| 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 | ||||
| 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 | ||||
| 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 | ||||
| 19. Ronde | 15.04.2024 | Sunderland AFC U21 | - | Middlesbrough FC U21 | 1:2 |  |
Engeland
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