| 2. Round | 18/08/2023 | Middlesbrough FC U21 | - | Everton FC U21 | 2:2 | ||||
| 3. Round | 25/08/2023 | Middlesbrough FC U21 | - | Wolverhampton Wanderers U21 | 3:2 |  |
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| 4. Round | 03/09/2023 | Liverpool FC U21 | - | Middlesbrough FC U21 | 1:4 | ||||
| 5. Round | 25/09/2023 | Leicester City U21 | - | Middlesbrough FC U21 | 1:3 | ||||
| 10. Round | 18/12/2023 | Reading FC U21 | - | Middlesbrough FC U21 | 2:2 | ||||
| 11. Round | 12/01/2024 | Arsenal FC U21 | - | Middlesbrough FC U21 | 1:0 | ||||
| 12. Round | 26/01/2024 | Middlesbrough FC U21 | - | West Bromwich Albion U21 | 0:1 | ||||
| 14. Round | 16/02/2024 | Aston Villa U21 | - | Middlesbrough FC U21 | 4:0 | |
England