| 5. Jornada | 14.09.2019 | Middlesbrough FC [Sub 18] | - | Wolverhampton Wanderers [Sub 18] | 2:0 |  |
|||
| 6. Jornada | 21.09.2019 | Liverpool FC [Sub 18] | - | Middlesbrough FC [Sub 18] | 3:0 | ||||
| 7. Jornada | 05.10.2019 | Middlesbrough FC [Sub 18] | - | Stoke City [Sub 18] | 1:1 | ||||
| 8. Jornada | 19.10.2019 | Manchester United [Sub 18] | - | Middlesbrough FC [Sub 18] | 1:1 | |
|||
| 9. Jornada | 02.11.2019 | Middlesbrough FC [Sub 18] | - | Sunderland AFC [Sub 18] | 4:3 | ||||
| 11. Jornada | 06.12.2019 | Middlesbrough FC [Sub 18] | - | West Bromwich Albion [Sub 18] | 3:2 | ||||
| 13. Jornada | 11.01.2020 | Everton FC [Sub 18] | - | Middlesbrough FC [Sub 18] | 1:0 | ||||
| 14. Jornada | 18.01.2020 | Middlesbrough FC [Sub 18] | - | Derby County [Sub 18] | 0:2 | ||||
| 10. Jornada | 25.01.2020 | Blackburn Rovers [Sub 18] | - | Middlesbrough FC [Sub 18] | 2:3 |
Inglaterra
Escocia