1. Round | 14/08/2023 | Nottingham Forest U23 | - | Middlesbrough FC U23 | 2:2 | ||||
7. Round | 27/10/2023 | West Ham United U23 | - | Middlesbrough FC U23 | 5:0 | ||||
8. Round | 05/11/2023 | Middlesbrough FC U23 | - | Derby County U23 | 1:0 | ||||
10. Round | 18/12/2023 | Reading FC U23 | - | Middlesbrough FC U23 | 2:2 | ||||
11. Round | 12/01/2024 | Arsenal FC U23 | - | Middlesbrough FC U23 | 1:0 | ||||
12. Round | 26/01/2024 | Middlesbrough FC U23 | - | West Bromwich Albion U23 | 0:1 | ||||
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 | ||||
18. Round | 08/04/2024 | Fulham FC U23 | - | Middlesbrough FC U23 | 2:2 | ||||
19. Round | 15/04/2024 | Sunderland AFC U23 | - | Middlesbrough FC U23 | 1:2 |