1. Round | 14/08/2023 | Nottingham Forest U23 | - | Middlesbrough FC U23 | 2:2 | ||||
5. Round | 25/09/2023 | Leicester City U23 | - | Middlesbrough FC U23 | 1:3 | ||||
6. Round | 29/09/2023 | Middlesbrough FC U23 | - | Stoke City U23 | 4:1 | ||||
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 | ||||
17. Round | 17/03/2024 | Middlesbrough FC U23 | - | Tottenham Hotspur U23 | 1:2 | ||||
19. Round | 15/04/2024 | Sunderland AFC U23 | - | Middlesbrough FC U23 | 1:2 | ||||
20. Round | 26/04/2024 | Middlesbrough FC U23 | - | Crystal Palace U23 | 2:3 |