1. Round | 14/08/2023 | Nottingham Forest U23 | - | Middlesbrough FC U23 | 2:2 | ||||
2. Round | 18/08/2023 | Middlesbrough FC U23 | - | Everton FC U23 | 2:2 | ||||
3. Round | 25/08/2023 | Middlesbrough FC U23 | - | Wolverhampton Wanderers U23 | 3:2 | ||||
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 | ||||
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 |