11. Round | 12/01/2024 | Arsenal FC U23 | - | Middlesbrough FC U23 | 1:0 | ||||
14. Round | 16/02/2024 | Aston Villa U23 | - | Middlesbrough FC U23 | 4:0 | ||||
9. Round | 23/02/2024 | Middlesbrough FC U23 | - | Chelsea FC U23 | 1:3 | ||||
15. Round | 01/03/2024 | Norwich City U23 | - | Middlesbrough FC U23 | 2:3 | ||||
16. Round | 08/03/2024 | Middlesbrough FC U23 | - | Manchester United U23 | 3:2 | ||||
17. Round | 17/03/2024 | Middlesbrough FC U23 | - | Tottenham Hotspur U23 | 1:2 |