| 8. Ronde | 05.11.2023 | Middlesbrough FC U21 | - | Derby County U21 | 1:0 | ||||
| 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 | ||||
| 9. Ronde | 23.02.2024 | Middlesbrough FC U21 | - | Chelsea FC U21 | 1:3 | ||||
| 16. Ronde | 08.03.2024 | Middlesbrough FC U21 | - | Manchester United U21 | 3:2 | ||||
| 17. Ronde | 17.03.2024 | Middlesbrough FC U21 | - | Tottenham Hotspur U21 | 1:2 | ||||
| 13. Ronde | 22.03.2024 | Middlesbrough FC U21 | - | Newcastle United U21 | 3:2 | ||||
| 18. Ronde | 08.04.2024 | Fulham FC U21 | - | Middlesbrough FC U21 | 2:2 | ||||
| 19. Ronde | 15.04.2024 | Sunderland AFC U21 | - | Middlesbrough FC U21 | 1:2 |
Engeland