4. Round | 03/09/2023 | Liverpool FC U23 | - | Middlesbrough FC U23 | 1:4 | ||||
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 | ||||
13. Round | 22/03/2024 | Middlesbrough FC U23 | - | Newcastle United U23 | 3:2 | ||||
19. Round | 15/04/2024 | Sunderland AFC U23 | - | Middlesbrough FC U23 | 1:2 |