| 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 |
England