| 1. Jornada | 10.08.2019 | Newcastle United [Sub 18] | - | Middlesbrough FC [Sub 18] | 3:3 | ||||
| 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 | ||||
| 15. Jornada | 01.02.2020 | Manchester City [Sub 18] | - | Middlesbrough FC [Sub 18] | 6:2 | |
|||
| 16. Jornada | 22.02.2020 | Wolverhampton Wanderers [Sub 18] | - | Middlesbrough FC [Sub 18] | 5:0 |
Inglaterra