| 2. Ronde | 18.08.2023 | Middlesbrough FC U21 | - | Everton FC U21 | 2:2 | ||||
| 3. Ronde | 25.08.2023 | Middlesbrough FC U21 | - | Wolverhampton Wanderers U21 | 3:2 |  |
|||
| 4. Ronde | 03.09.2023 | Liverpool FC U21 | - | Middlesbrough FC U21 | 1:4 | ||||
| 5. Ronde | 25.09.2023 | Leicester City U21 | - | Middlesbrough FC U21 | 1:3 | ||||
| 10. Ronde | 18.12.2023 | Reading FC U21 | - | Middlesbrough FC U21 | 2:2 | ||||
| 11. Ronde | 12.01.2024 | Arsenal FC U21 | - | Middlesbrough FC U21 | 1:0 | ||||
| 12. Ronde | 26.01.2024 | Middlesbrough FC U21 | - | West Bromwich Albion U21 | 0:1 | ||||
| 14. Ronde | 16.02.2024 | Aston Villa U21 | - | Middlesbrough FC U21 | 4:0 | |
Engeland