| 7. Round | 27/10/2023 | West Ham United U21 | - | Middlesbrough FC U21 | 5:0 | ||||
| 8. Round | 05/11/2023 | Middlesbrough FC U21 | - | Derby County U21 | 1:0 | ||||
| 11. Round | 12/01/2024 | Arsenal FC U21 | - | Middlesbrough FC U21 | 1:0 | ||||
| 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 | ||||
| 16. Round | 08/03/2024 | Middlesbrough FC U21 | - | Manchester United U21 | 3:2 |  |
|||
| 17. Round | 17/03/2024 | Middlesbrough FC U21 | - | Tottenham Hotspur U21 | 1:2 |  |
|||
| 13. Round | 22/03/2024 | Middlesbrough FC U21 | - | Newcastle United U21 | 3:2 | ||||
| 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 | |
|
||
| 20. Round | 26/04/2024 | Middlesbrough FC U21 | - | Crystal Palace U21 | 2:3 | |
Kenya
Germany