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 | ||||
4. Round | 03/09/2023 | Liverpool FC U23 | - | Middlesbrough FC U23 | 1:4 | ||||
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 | ||||
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 | ||||
20. Round | 26/04/2024 | Middlesbrough FC U23 | - | Crystal Palace U23 | 2:3 |