| 3. Jornada | 25.08.2018 | Everton FC [Sub 18] | - | Middlesbrough FC [Sub 18] | 2:1 |  |
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| 5. Jornada | 15.09.2018 | Derby County [Sub 18] | - | Middlesbrough FC [Sub 18] | 3:2 | |
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| 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 | ||||
| 8. Jornada | 20.03.2019 | Middlesbrough FC [Sub 18] | - | Blackburn Rovers [Sub 18] | 2:2 | |
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| 19. Jornada | 23.03.2019 | Middlesbrough FC [Sub 18] | - | Manchester City [Sub 18] | 4:2 | ||||
| 22. Jornada | 04.05.2019 | Liverpool FC [Sub 18] | - | Middlesbrough FC [Sub 18] | 1:0 |
Inglaterra