| 2. Jornada | 18.08.2018 | Middlesbrough FC [Sub 18] | - | Stoke City [Sub 18] | 2:0 | ||||
| 4. Jornada | 01.09.2018 | Middlesbrough FC [Sub 18] | - | Manchester United [Sub 18] | 3:1 |  |
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| 5. Jornada | 15.09.2018 | Derby County [Sub 18] | - | Middlesbrough FC [Sub 18] | 3:2 | ||||
| 10. Jornada | 24.11.2018 | Newcastle United [Sub 18] | - | Middlesbrough FC [Sub 18] | 2:3 |  |
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| 11. Jornada | 01.12.2018 | Middlesbrough FC [Sub 18] | - | Liverpool FC [Sub 18] | 5:6 | |
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| 9. Jornada | 04.12.2018 | Manchester City [Sub 18] | - | Middlesbrough FC [Sub 18] | 6:0 | ||||
| 16. Jornada | 23.02.2019 | Middlesbrough FC [Sub 18] | - | Derby County [Sub 18] | 0:2 | ||||
| 17. Jornada | 02.03.2019 | Sunderland AFC [Sub 18] | - | Middlesbrough FC [Sub 18] | 2:8 | |
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| 8. Jornada | 20.03.2019 | Middlesbrough FC [Sub 18] | - | Blackburn Rovers [Sub 18] | 2:2 | ||||
| 19. Jornada | 23.03.2019 | Middlesbrough FC [Sub 18] | - | Manchester City [Sub 18] | 4:2 | ||||
| 20. Jornada | 06.04.2019 | Blackburn Rovers [Sub 18] | - | Middlesbrough FC [Sub 18] | 3:1 | ||||
| 21. Jornada | 13.04.2019 | Middlesbrough FC [Sub 18] | - | Newcastle United [Sub 18] | 4:1 |
Inglaterra