| 1. Round | 14/08/2023 | Nottingham Forest U21 | - | Middlesbrough FC U21 | 2:2 | ||||
| 2. Round | 18/08/2023 | Middlesbrough FC U21 | - | Everton FC U21 | 2:2 |  |
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| 3. Round | 25/08/2023 | Middlesbrough FC U21 | - | Wolverhampton Wanderers U21 | 3:2 | ||||
| 14. Round | 16/02/2024 | Aston Villa U21 | - | Middlesbrough FC U21 | 4:0 | ||||
| 9. Round | 23/02/2024 | Middlesbrough FC U21 | - | Chelsea FC U21 | 1:3 | ||||
| 15. Round | 01/03/2024 | Norwich City U21 | - | Middlesbrough FC U21 | 2:3 | ||||
| 18. Round | 08/04/2024 | Fulham FC U21 | - | Middlesbrough FC U21 | 2:2 | ||||
| 19. Round | 15/04/2024 | Sunderland AFC U21 | - | Middlesbrough FC U21 | 1:2 |  |
England
Ghana